Resolve merge conflict

2022-03-02 08:11:50 +00:00 · 2022-03-02 08:11:50 +00:00 · 5b169010be
parent 49cd761bf6 eeded85d9c
commit 5b169010be
23 changed files with 681 additions and 510 deletions
--- a/.golangci.yaml
+++ b/.golangci.yaml
@ -29,6 +29,7 @@ linters:
    - wrapcheck
    - dupl
    - makezero
+    - maintidx

    # We might want to enable this, but it might be a lot of work
    - cyclop
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@ -1,31 +1,37 @@
 # CHANGELOG

-**0.15.0 (2022-xx-xx):**
+## 0.15.0 (2022-xx-xx)

-**BREAKING**:
+**Note:** Take a backup of your database before upgrading.
+
+### BREAKING

 - Boundaries between Namespaces has been removed and all nodes can communicate by default [#357](https://github.com/juanfont/headscale/pull/357)
  - To limit access between nodes, use [ACLs](./docs/acls.md).

-**Features**:
+### Features

 - Add support for writing ACL files with YAML [#359](https://github.com/juanfont/headscale/pull/359)
+- Users can now use emails in ACL's groups [#372](https://github.com/juanfont/headscale/issues/372)

-**Changes**:
+### Changes

 - Fix a bug were the same IP could be assigned to multiple hosts if joined in quick succession [#346](https://github.com/juanfont/headscale/pull/346)
+- Simplify the code behind registration of machines [#366](https://github.com/juanfont/headscale/pull/366)
+  - Nodes are now only written to database if they are registrated successfully
+- Fix a limitation in the ACLs that prevented users to write rules with `*` as source [#374](https://github.com/juanfont/headscale/issues/374)

-**0.14.0 (2022-02-24):**
+## 0.14.0 (2022-02-24)

-**UPCOMING BREAKING**:
-From the **next** version (`0.15.0`), all machines will be able to communicate regardless of
+**UPCOMING ### BREAKING
+From the **next\*\* version (`0.15.0`), all machines will be able to communicate regardless of
 if they are in the same namespace. This means that the behaviour currently limited to ACLs
 will become default. From version `0.15.0`, all limitation of communications must be done
 with ACLs.

 This is a part of aligning `headscale`'s behaviour with Tailscale's upstream behaviour.

-**BREAKING**:
+### BREAKING

 - ACLs have been rewritten to align with the bevaviour Tailscale Control Panel provides. **NOTE:** This is only active if you use ACLs
  - Namespaces are now treated as Users
@ -33,17 +39,17 @@ This is a part of aligning `headscale`'s behaviour with Tailscale's upstream beh
  - Tags should now work correctly and adding a host to Headscale should now reload the rules.
  - The documentation have a [fictional example](docs/acls.md) that should cover some use cases of the ACLs features

-**Features**:
+### Features

 - Add support for configurable mTLS [docs](docs/tls.md#configuring-mutual-tls-authentication-mtls) [#297](https://github.com/juanfont/headscale/pull/297)

-**Changes**:
+### Changes

 - Remove dependency on CGO (switch from CGO SQLite to pure Go) [#346](https://github.com/juanfont/headscale/pull/346)

 **0.13.0 (2022-02-18):**

-**Features**:
+### Features

 - Add IPv6 support to the prefix assigned to namespaces
 - Add API Key support
@ -54,7 +60,7 @@ This is a part of aligning `headscale`'s behaviour with Tailscale's upstream beh
  - `oidc.domain_map` option has been removed
  - `strip_email_domain` option has been added (see [config-example.yaml](./config_example.yaml))

-**Changes**:
+### Changes

 - `ip_prefix` is now superseded by `ip_prefixes` in the configuration [#208](https://github.com/juanfont/headscale/pull/208)
 - Upgrade `tailscale` (1.20.4) and other dependencies to latest [#314](https://github.com/juanfont/headscale/pull/314)
@ -63,35 +69,35 @@ This is a part of aligning `headscale`'s behaviour with Tailscale's upstream beh

 **0.12.4 (2022-01-29):**

-**Changes**:
+### Changes

 - Make gRPC Unix Socket permissions configurable [#292](https://github.com/juanfont/headscale/pull/292)
 - Trim whitespace before reading Private Key from file [#289](https://github.com/juanfont/headscale/pull/289)
 - Add new command to generate a private key for `headscale` [#290](https://github.com/juanfont/headscale/pull/290)
 - Fixed issue where hosts deleted from control server may be written back to the database, as long as they are connected to the control server [#278](https://github.com/juanfont/headscale/pull/278)

-**0.12.3 (2022-01-13):**
+## 0.12.3 (2022-01-13)

-**Changes**:
+### Changes

 - Added Alpine container [#270](https://github.com/juanfont/headscale/pull/270)
 - Minor updates in dependencies [#271](https://github.com/juanfont/headscale/pull/271)

-**0.12.2 (2022-01-11):**
+## 0.12.2 (2022-01-11)

 Happy New Year!

-**Changes**:
+### Changes

 - Fix Docker release [#258](https://github.com/juanfont/headscale/pull/258)
 - Rewrite main docs [#262](https://github.com/juanfont/headscale/pull/262)
 - Improve Docker docs [#263](https://github.com/juanfont/headscale/pull/263)

-**0.12.1 (2021-12-24):**
+## 0.12.1 (2021-12-24)

 (We are skipping 0.12.0 to correct a mishap done weeks ago with the version tagging)

-**BREAKING**:
+### BREAKING

 - Upgrade to Tailscale 1.18 [#229](https://github.com/juanfont/headscale/pull/229)
  - This change requires a new format for private key, private keys are now generated automatically:
@ -99,19 +105,19 @@ Happy New Year!
    2. Restart `headscale`, a new key will be generated.
    3. Restart all Tailscale clients to fetch the new key

-**Changes**:
+### Changes

 - Unify configuration example [#197](https://github.com/juanfont/headscale/pull/197)
 - Add stricter linting and formatting [#223](https://github.com/juanfont/headscale/pull/223)

-**Features**:
+### Features

 - Add gRPC and HTTP API (HTTP API is currently disabled) [#204](https://github.com/juanfont/headscale/pull/204)
 - Use gRPC between the CLI and the server [#206](https://github.com/juanfont/headscale/pull/206), [#212](https://github.com/juanfont/headscale/pull/212)
 - Beta OpenID Connect support [#126](https://github.com/juanfont/headscale/pull/126), [#227](https://github.com/juanfont/headscale/pull/227)

-**0.11.0 (2021-10-25):**
+## 0.11.0 (2021-10-25)

-**BREAKING**:
+### BREAKING

 - Make headscale fetch DERP map from URL and file [#196](https://github.com/juanfont/headscale/pull/196)
--- a/acls.go
+++ b/acls.go
@ -160,7 +160,7 @@ func (h *Headscale) generateACLPolicySrcIP(
 	aclPolicy ACLPolicy,
 	u string,
 ) ([]string, error) {
-	return expandAlias(machines, aclPolicy, u)
+	return expandAlias(machines, aclPolicy, u, h.cfg.OIDC.StripEmaildomain)
 }

 func (h *Headscale) generateACLPolicyDestPorts(
@ -186,7 +186,12 @@ func (h *Headscale) generateACLPolicyDestPorts(
 		alias = fmt.Sprintf("%s:%s", tokens[0], tokens[1])
 	}

-	expanded, err := expandAlias(machines, aclPolicy, alias)
+	expanded, err := expandAlias(
+		machines,
+		aclPolicy,
+		alias,
+		h.cfg.OIDC.StripEmaildomain,
+	)
 	if err != nil {
 		return nil, err
 	}
@ -218,6 +223,7 @@ func expandAlias(
 	machines []Machine,
 	aclPolicy ACLPolicy,
 	alias string,
+	stripEmailDomain bool,
 ) ([]string, error) {
 	ips := []string{}
 	if alias == "*" {
@ -225,7 +231,7 @@ func expandAlias(
 	}

 	if strings.HasPrefix(alias, "group:") {
-		namespaces, err := expandGroup(aclPolicy, alias)
+		namespaces, err := expandGroup(aclPolicy, alias, stripEmailDomain)
 		if err != nil {
 			return ips, err
 		}
@ -240,7 +246,7 @@ func expandAlias(
 	}

 	if strings.HasPrefix(alias, "tag:") {
-		owners, err := expandTagOwners(aclPolicy, alias)
+		owners, err := expandTagOwners(aclPolicy, alias, stripEmailDomain)
 		if err != nil {
 			return ips, err
 		}
@ -383,7 +389,11 @@ func filterMachinesByNamespace(machines []Machine, namespace string) []Machine {

 // expandTagOwners will return a list of namespace. An owner can be either a namespace or a group
 // a group cannot be composed of groups.
-func expandTagOwners(aclPolicy ACLPolicy, tag string) ([]string, error) {
+func expandTagOwners(
+	aclPolicy ACLPolicy,
+	tag string,
+	stripEmailDomain bool,
+) ([]string, error) {
 	var owners []string
 	ows, ok := aclPolicy.TagOwners[tag]
 	if !ok {
@ -395,7 +405,7 @@ func expandTagOwners(aclPolicy ACLPolicy, tag string) ([]string, error) {
 	}
 	for _, owner := range ows {
 		if strings.HasPrefix(owner, "group:") {
-			gs, err := expandGroup(aclPolicy, owner)
+			gs, err := expandGroup(aclPolicy, owner, stripEmailDomain)
 			if err != nil {
 				return []string{}, err
 			}
@ -410,8 +420,13 @@ func expandTagOwners(aclPolicy ACLPolicy, tag string) ([]string, error) {

 // expandGroup will return the list of namespace inside the group
 // after some validation.
-func expandGroup(aclPolicy ACLPolicy, group string) ([]string, error) {
-	groups, ok := aclPolicy.Groups[group]
+func expandGroup(
+	aclPolicy ACLPolicy,
+	group string,
+	stripEmailDomain bool,
+) ([]string, error) {
+	outGroups := []string{}
+	aclGroups, ok := aclPolicy.Groups[group]
 	if !ok {
 		return []string{}, fmt.Errorf(
 			"group %v isn't registered. %w",
@ -419,14 +434,23 @@ func expandGroup(aclPolicy ACLPolicy, group string) ([]string, error) {
 			errInvalidGroup,
 		)
 	}
-	for _, g := range groups {
-		if strings.HasPrefix(g, "group:") {
+	for _, group := range aclGroups {
+		if strings.HasPrefix(group, "group:") {
 			return []string{}, fmt.Errorf(
 				"%w. A group cannot be composed of groups. https://tailscale.com/kb/1018/acls/#groups",
 				errInvalidGroup,
 			)
 		}
+		grp, err := NormalizeNamespaceName(group, stripEmailDomain)
+		if err != nil {
+			return []string{}, fmt.Errorf(
+				"failed to normalize group %q, err: %w",
+				group,
+				errInvalidGroup,
+			)
+		}
+		outGroups = append(outGroups, grp)
 	}

-	return groups, nil
+	return outGroups, nil
 }
--- a/acls_test.go
+++ b/acls_test.go
@ -121,7 +121,6 @@ func (s *Suite) TestValidExpandTagOwnersInUsers(c *check.C) {
 		Name:           "testmachine",
 		IPAddresses:    MachineAddresses{netaddr.MustParseIP("100.64.0.1")},
 		NamespaceID:    namespace.ID,
-		Registered:     true,
 		RegisterMethod: RegisterMethodAuthKey,
 		AuthKeyID:      uint(pak.ID),
 		HostInfo:       HostInfo(hostInfo),
@ -168,7 +167,6 @@ func (s *Suite) TestValidExpandTagOwnersInPorts(c *check.C) {
 		Name:           "testmachine",
 		IPAddresses:    MachineAddresses{netaddr.MustParseIP("100.64.0.1")},
 		NamespaceID:    namespace.ID,
-		Registered:     true,
 		RegisterMethod: RegisterMethodAuthKey,
 		AuthKeyID:      uint(pak.ID),
 		HostInfo:       HostInfo(hostInfo),
@ -215,7 +213,6 @@ func (s *Suite) TestInvalidTagValidNamespace(c *check.C) {
 		Name:           "testmachine",
 		IPAddresses:    MachineAddresses{netaddr.MustParseIP("100.64.0.1")},
 		NamespaceID:    namespace.ID,
-		Registered:     true,
 		RegisterMethod: RegisterMethodAuthKey,
 		AuthKeyID:      uint(pak.ID),
 		HostInfo:       HostInfo(hostInfo),
@ -261,7 +258,6 @@ func (s *Suite) TestValidTagInvalidNamespace(c *check.C) {
 		Name:           "webserver",
 		IPAddresses:    MachineAddresses{netaddr.MustParseIP("100.64.0.1")},
 		NamespaceID:    namespace.ID,
-		Registered:     true,
 		RegisterMethod: RegisterMethodAuthKey,
 		AuthKeyID:      uint(pak.ID),
 		HostInfo:       HostInfo(hostInfo),
@ -281,7 +277,6 @@ func (s *Suite) TestValidTagInvalidNamespace(c *check.C) {
 		Name:           "user",
 		IPAddresses:    MachineAddresses{netaddr.MustParseIP("100.64.0.2")},
 		NamespaceID:    namespace.ID,
-		Registered:     true,
 		RegisterMethod: RegisterMethodAuthKey,
 		AuthKeyID:      uint(pak.ID),
 		HostInfo:       HostInfo(hostInfo2),
@ -375,7 +370,6 @@ func (s *Suite) TestPortNamespace(c *check.C) {
 		DiscoKey:       "faa",
 		Name:           "testmachine",
 		NamespaceID:    namespace.ID,
-		Registered:     true,
 		RegisterMethod: RegisterMethodAuthKey,
 		IPAddresses:    ips,
 		AuthKeyID:      uint(pak.ID),
@ -418,7 +412,6 @@ func (s *Suite) TestPortGroup(c *check.C) {
 		DiscoKey:       "faa",
 		Name:           "testmachine",
 		NamespaceID:    namespace.ID,
-		Registered:     true,
 		RegisterMethod: RegisterMethodAuthKey,
 		IPAddresses:    ips,
 		AuthKeyID:      uint(pak.ID),
@ -444,8 +437,9 @@ func (s *Suite) TestPortGroup(c *check.C) {

 func Test_expandGroup(t *testing.T) {
 	type args struct {
-		aclPolicy ACLPolicy
-		group     string
+		aclPolicy        ACLPolicy
+		group            string
+		stripEmailDomain bool
 	}
 	tests := []struct {
 		name    string
@ -462,7 +456,8 @@ func Test_expandGroup(t *testing.T) {
 						"group:foo":  []string{"user2", "user3"},
 					},
 				},
-				group: "group:test",
+				group:            "group:test",
+				stripEmailDomain: true,
 			},
 			want:    []string{"user1", "user2", "user3"},
 			wantErr: false,
@ -476,15 +471,54 @@ func Test_expandGroup(t *testing.T) {
 						"group:foo":  []string{"user2", "user3"},
 					},
 				},
-				group: "group:undefined",
+				group:            "group:undefined",
+				stripEmailDomain: true,
 			},
 			want:    []string{},
 			wantErr: true,
 		},
+		{
+			name: "Expand emails in group",
+			args: args{
+				aclPolicy: ACLPolicy{
+					Groups: Groups{
+						"group:admin": []string{
+							"joe.bar@gmail.com",
+							"john.doe@yahoo.fr",
+						},
+					},
+				},
+				group:            "group:admin",
+				stripEmailDomain: true,
+			},
+			want:    []string{"joe.bar", "john.doe"},
+			wantErr: false,
+		},
+		{
+			name: "Expand emails in group",
+			args: args{
+				aclPolicy: ACLPolicy{
+					Groups: Groups{
+						"group:admin": []string{
+							"joe.bar@gmail.com",
+							"john.doe@yahoo.fr",
+						},
+					},
+				},
+				group:            "group:admin",
+				stripEmailDomain: false,
+			},
+			want:    []string{"joe.bar.gmail.com", "john.doe.yahoo.fr"},
+			wantErr: false,
+		},
 	}
 	for _, test := range tests {
 		t.Run(test.name, func(t *testing.T) {
-			got, err := expandGroup(test.args.aclPolicy, test.args.group)
+			got, err := expandGroup(
+				test.args.aclPolicy,
+				test.args.group,
+				test.args.stripEmailDomain,
+			)
 			if (err != nil) != test.wantErr {
 				t.Errorf("expandGroup() error = %v, wantErr %v", err, test.wantErr)

@ -499,8 +533,9 @@ func Test_expandGroup(t *testing.T) {

 func Test_expandTagOwners(t *testing.T) {
 	type args struct {
-		aclPolicy ACLPolicy
-		tag       string
+		aclPolicy        ACLPolicy
+		tag              string
+		stripEmailDomain bool
 	}
 	tests := []struct {
 		name    string
@ -514,7 +549,8 @@ func Test_expandTagOwners(t *testing.T) {
 				aclPolicy: ACLPolicy{
 					TagOwners: TagOwners{"tag:test": []string{"user1"}},
 				},
-				tag: "tag:test",
+				tag:              "tag:test",
+				stripEmailDomain: true,
 			},
 			want:    []string{"user1"},
 			wantErr: false,
@ -526,7 +562,8 @@ func Test_expandTagOwners(t *testing.T) {
 					Groups:    Groups{"group:foo": []string{"user1", "user2"}},
 					TagOwners: TagOwners{"tag:test": []string{"group:foo"}},
 				},
-				tag: "tag:test",
+				tag:              "tag:test",
+				stripEmailDomain: true,
 			},
 			want:    []string{"user1", "user2"},
 			wantErr: false,
@ -538,7 +575,8 @@ func Test_expandTagOwners(t *testing.T) {
 					Groups:    Groups{"group:foo": []string{"user1", "user2"}},
 					TagOwners: TagOwners{"tag:test": []string{"group:foo", "user3"}},
 				},
-				tag: "tag:test",
+				tag:              "tag:test",
+				stripEmailDomain: true,
 			},
 			want:    []string{"user1", "user2", "user3"},
 			wantErr: false,
@ -549,7 +587,8 @@ func Test_expandTagOwners(t *testing.T) {
 				aclPolicy: ACLPolicy{
 					TagOwners: TagOwners{"tag:foo": []string{"group:foo", "user1"}},
 				},
-				tag: "tag:test",
+				tag:              "tag:test",
+				stripEmailDomain: true,
 			},
 			want:    []string{},
 			wantErr: true,
@ -561,7 +600,8 @@ func Test_expandTagOwners(t *testing.T) {
 					Groups:    Groups{"group:bar": []string{"user1", "user2"}},
 					TagOwners: TagOwners{"tag:test": []string{"group:foo", "user2"}},
 				},
-				tag: "tag:test",
+				tag:              "tag:test",
+				stripEmailDomain: true,
 			},
 			want:    []string{},
 			wantErr: true,
@ -569,7 +609,11 @@ func Test_expandTagOwners(t *testing.T) {
 	}
 	for _, test := range tests {
 		t.Run(test.name, func(t *testing.T) {
-			got, err := expandTagOwners(test.args.aclPolicy, test.args.tag)
+			got, err := expandTagOwners(
+				test.args.aclPolicy,
+				test.args.tag,
+				test.args.stripEmailDomain,
+			)
 			if (err != nil) != test.wantErr {
 				t.Errorf("expandTagOwners() error = %v, wantErr %v", err, test.wantErr)

@ -731,9 +775,10 @@ func Test_listMachinesInNamespace(t *testing.T) {
 // nolint
 func Test_expandAlias(t *testing.T) {
 	type args struct {
-		machines  []Machine
-		aclPolicy ACLPolicy
-		alias     string
+		machines         []Machine
+		aclPolicy        ACLPolicy
+		alias            string
+		stripEmailDomain bool
 	}
 	tests := []struct {
 		name    string
@ -753,7 +798,8 @@ func Test_expandAlias(t *testing.T) {
 						},
 					},
 				},
-				aclPolicy: ACLPolicy{},
+				aclPolicy:        ACLPolicy{},
+				stripEmailDomain: true,
 			},
 			want:    []string{"*"},
 			wantErr: false,
@ -791,6 +837,7 @@ func Test_expandAlias(t *testing.T) {
 				aclPolicy: ACLPolicy{
 					Groups: Groups{"group:accountant": []string{"joe", "marc"}},
 				},
+				stripEmailDomain: true,
 			},
 			want:    []string{"100.64.0.1", "100.64.0.2", "100.64.0.3"},
 			wantErr: false,
@ -828,6 +875,7 @@ func Test_expandAlias(t *testing.T) {
 				aclPolicy: ACLPolicy{
 					Groups: Groups{"group:accountant": []string{"joe", "marc"}},
 				},
+				stripEmailDomain: true,
 			},
 			want:    []string{},
 			wantErr: true,
@ -835,9 +883,10 @@ func Test_expandAlias(t *testing.T) {
 		{
 			name: "simple ipaddress",
 			args: args{
-				alias:     "10.0.0.3",
-				machines:  []Machine{},
-				aclPolicy: ACLPolicy{},
+				alias:            "10.0.0.3",
+				machines:         []Machine{},
+				aclPolicy:        ACLPolicy{},
+				stripEmailDomain: true,
 			},
 			want:    []string{"10.0.0.3"},
 			wantErr: false,
@ -852,6 +901,7 @@ func Test_expandAlias(t *testing.T) {
 						"homeNetwork": netaddr.MustParseIPPrefix("192.168.1.0/24"),
 					},
 				},
+				stripEmailDomain: true,
 			},
 			want:    []string{"192.168.1.0/24"},
 			wantErr: false,
@ -859,9 +909,10 @@ func Test_expandAlias(t *testing.T) {
 		{
 			name: "simple host",
 			args: args{
-				alias:     "10.0.0.1",
-				machines:  []Machine{},
-				aclPolicy: ACLPolicy{},
+				alias:            "10.0.0.1",
+				machines:         []Machine{},
+				aclPolicy:        ACLPolicy{},
+				stripEmailDomain: true,
 			},
 			want:    []string{"10.0.0.1"},
 			wantErr: false,
@ -869,9 +920,10 @@ func Test_expandAlias(t *testing.T) {
 		{
 			name: "simple CIDR",
 			args: args{
-				alias:     "10.0.0.0/16",
-				machines:  []Machine{},
-				aclPolicy: ACLPolicy{},
+				alias:            "10.0.0.0/16",
+				machines:         []Machine{},
+				aclPolicy:        ACLPolicy{},
+				stripEmailDomain: true,
 			},
 			want:    []string{"10.0.0.0/16"},
 			wantErr: false,
@ -919,6 +971,7 @@ func Test_expandAlias(t *testing.T) {
 				aclPolicy: ACLPolicy{
 					TagOwners: TagOwners{"tag:hr-webserver": []string{"joe"}},
 				},
+				stripEmailDomain: true,
 			},
 			want:    []string{"100.64.0.1", "100.64.0.2"},
 			wantErr: false,
@ -959,6 +1012,7 @@ func Test_expandAlias(t *testing.T) {
 						"tag:accountant-webserver": []string{"group:accountant"},
 					},
 				},
+				stripEmailDomain: true,
 			},
 			want:    []string{},
 			wantErr: true,
@ -1006,6 +1060,7 @@ func Test_expandAlias(t *testing.T) {
 				aclPolicy: ACLPolicy{
 					TagOwners: TagOwners{"tag:accountant-webserver": []string{"joe"}},
 				},
+				stripEmailDomain: true,
 			},
 			want:    []string{"100.64.0.4"},
 			wantErr: false,
@ -1017,6 +1072,7 @@ func Test_expandAlias(t *testing.T) {
 				test.args.machines,
 				test.args.aclPolicy,
 				test.args.alias,
+				test.args.stripEmailDomain,
 			)
 			if (err != nil) != test.wantErr {
 				t.Errorf("expandAlias() error = %v, wantErr %v", err, test.wantErr)
--- a/api.go
+++ b/api.go
@ -22,7 +22,7 @@ import (

 const (
 	reservedResponseHeaderSize               = 4
-	RegisterMethodAuthKey                    = "authKey"
+	RegisterMethodAuthKey                    = "authkey"
 	RegisterMethodOIDC                       = "oidc"
 	RegisterMethodCLI                        = "cli"
 	ErrRegisterMethodCLIDoesNotSupportExpire = Error(
@ -125,25 +125,50 @@ func (h *Headscale) RegistrationHandler(ctx *gin.Context) {
 	machine, err := h.GetMachineByMachineKey(machineKey)
 	if errors.Is(err, gorm.ErrRecordNotFound) {
 		log.Info().Str("machine", req.Hostinfo.Hostname).Msg("New machine")
-		newMachine := Machine{
-			Expiry:     &time.Time{},
-			MachineKey: MachinePublicKeyStripPrefix(machineKey),
-			Name:       req.Hostinfo.Hostname,
-		}
-		if err := h.db.Create(&newMachine).Error; err != nil {
-			log.Error().
-				Caller().
-				Err(err).
-				Msg("Could not create row")
-			machineRegistrations.WithLabelValues("unknown", "web", "error", machine.Namespace.Name).
-				Inc()
+
+		machineKeyStr := MachinePublicKeyStripPrefix(machineKey)
+
+		// If the machine has AuthKey set, handle registration via PreAuthKeys
+		if req.Auth.AuthKey != "" {
+			h.handleAuthKey(ctx, machineKey, req)

 			return
 		}
-		machine = &newMachine
+
+		// The machine did not have a key to authenticate, which means
+		// that we rely on a method that calls back some how (OpenID or CLI)
+		// We create the machine and then keep it around until a callback
+		// happens
+		newMachine := Machine{
+			MachineKey: machineKeyStr,
+			Name:       req.Hostinfo.Hostname,
+			NodeKey:    NodePublicKeyStripPrefix(req.NodeKey),
+			LastSeen:   &now,
+			Expiry:     &time.Time{},
+		}
+
+		if !req.Expiry.IsZero() {
+			log.Trace().
+				Caller().
+				Str("machine", req.Hostinfo.Hostname).
+				Time("expiry", req.Expiry).
+				Msg("Non-zero expiry time requested")
+			newMachine.Expiry = &req.Expiry
+		}
+
+		h.registrationCache.Set(
+			machineKeyStr,
+			newMachine,
+			registerCacheExpiration,
+		)
+
+		h.handleMachineRegistrationNew(ctx, machineKey, req)
+
+		return
 	}

-	if machine.Registered {
+	// The machine is already registered, so we need to pass through reauth or key update.
+	if machine != nil {
 		// If the NodeKey stored in headscale is the same as the key presented in a registration
 		// request, then we have a node that is either:
 		// - Trying to log out (sending a expiry in the past)
@ -180,15 +205,6 @@ func (h *Headscale) RegistrationHandler(ctx *gin.Context) {

 		return
 	}
-
-	// If the machine has AuthKey set, handle registration via PreAuthKeys
-	if req.Auth.AuthKey != "" {
-		h.handleAuthKey(ctx, machineKey, req, *machine)
-
-		return
-	}
-
-	h.handleMachineRegistrationNew(ctx, machineKey, req, *machine)
 }

 func (h *Headscale) getMapResponse(
@ -402,7 +418,7 @@ func (h *Headscale) handleMachineExpired(
 		Msg("Machine registration has expired. Sending a authurl to register")

 	if registerRequest.Auth.AuthKey != "" {
-		h.handleAuthKey(ctx, machineKey, registerRequest, machine)
+		h.handleAuthKey(ctx, machineKey, registerRequest)

 		return
 	}
@ -465,13 +481,12 @@ func (h *Headscale) handleMachineRegistrationNew(
 	ctx *gin.Context,
 	machineKey key.MachinePublic,
 	registerRequest tailcfg.RegisterRequest,
-	machine Machine,
 ) {
 	resp := tailcfg.RegisterResponse{}

 	// The machine registration is new, redirect the client to the registration URL
 	log.Debug().
-		Str("machine", machine.Name).
+		Str("machine", registerRequest.Hostinfo.Hostname).
 		Msg("The node is sending us a new NodeKey, sending auth url")
 	if h.cfg.OIDC.Issuer != "" {
 		resp.AuthURL = fmt.Sprintf(
@ -484,24 +499,6 @@ func (h *Headscale) handleMachineRegistrationNew(
 			strings.TrimSuffix(h.cfg.ServerURL, "/"), MachinePublicKeyStripPrefix(machineKey))
 	}

-	if !registerRequest.Expiry.IsZero() {
-		log.Trace().
-			Caller().
-			Str("machine", machine.Name).
-			Time("expiry", registerRequest.Expiry).
-			Msg("Non-zero expiry time requested, adding to cache")
-		h.requestedExpiryCache.Set(
-			machineKey.String(),
-			registerRequest.Expiry,
-			requestedExpiryCacheExpiration,
-		)
-	}
-
-	machine.NodeKey = NodePublicKeyStripPrefix(registerRequest.NodeKey)
-
-	// save the NodeKey
-	h.db.Save(&machine)
-
 	respBody, err := encode(resp, &machineKey, h.privateKey)
 	if err != nil {
 		log.Error().
@ -520,19 +517,21 @@ func (h *Headscale) handleAuthKey(
 	ctx *gin.Context,
 	machineKey key.MachinePublic,
 	registerRequest tailcfg.RegisterRequest,
-	machine Machine,
 ) {
+	machineKeyStr := MachinePublicKeyStripPrefix(machineKey)
+
 	log.Debug().
 		Str("func", "handleAuthKey").
 		Str("machine", registerRequest.Hostinfo.Hostname).
 		Msgf("Processing auth key for %s", registerRequest.Hostinfo.Hostname)
 	resp := tailcfg.RegisterResponse{}
+
 	pak, err := h.checkKeyValidity(registerRequest.Auth.AuthKey)
 	if err != nil {
 		log.Error().
 			Caller().
 			Str("func", "handleAuthKey").
-			Str("machine", machine.Name).
+			Str("machine", registerRequest.Hostinfo.Hostname).
 			Err(err).
 			Msg("Failed authentication via AuthKey")
 		resp.MachineAuthorized = false
@ -541,76 +540,66 @@ func (h *Headscale) handleAuthKey(
 			log.Error().
 				Caller().
 				Str("func", "handleAuthKey").
-				Str("machine", machine.Name).
+				Str("machine", registerRequest.Hostinfo.Hostname).
 				Err(err).
 				Msg("Cannot encode message")
 			ctx.String(http.StatusInternalServerError, "")
-			machineRegistrations.WithLabelValues("new", "authkey", "error", machine.Namespace.Name).
+			machineRegistrations.WithLabelValues("new", RegisterMethodAuthKey, "error", pak.Namespace.Name).
 				Inc()

 			return
 		}
+
 		ctx.Data(http.StatusUnauthorized, "application/json; charset=utf-8", respBody)
 		log.Error().
 			Caller().
 			Str("func", "handleAuthKey").
-			Str("machine", machine.Name).
+			Str("machine", registerRequest.Hostinfo.Hostname).
 			Msg("Failed authentication via AuthKey")
-		machineRegistrations.WithLabelValues("new", "authkey", "error", machine.Namespace.Name).
+		machineRegistrations.WithLabelValues("new", RegisterMethodAuthKey, "error", pak.Namespace.Name).
 			Inc()

 		return
 	}

-	if machine.isRegistered() {
-		log.Trace().
-			Caller().
-			Str("machine", machine.Name).
-			Msg("machine already registered, reauthenticating")
+	log.Debug().
+		Str("func", "handleAuthKey").
+		Str("machine", registerRequest.Hostinfo.Hostname).
+		Msg("Authentication key was valid, proceeding to acquire IP addresses")

-		h.RefreshMachine(&machine, registerRequest.Expiry)
-	} else {
-		log.Debug().
-			Str("func", "handleAuthKey").
-			Str("machine", machine.Name).
-			Msg("Authentication key was valid, proceeding to acquire IP addresses")
+	nodeKey := NodePublicKeyStripPrefix(registerRequest.NodeKey)
+	now := time.Now().UTC()

-		h.ipAllocationMutex.Lock()
-
-		ips, err := h.getAvailableIPs()
-		if err != nil {
-			log.Error().
-				Caller().
-				Str("func", "handleAuthKey").
-				Str("machine", machine.Name).
-				Msg("Failed to find an available IP address")
-			machineRegistrations.WithLabelValues("new", "authkey", "error", machine.Namespace.Name).
-				Inc()
-
-			return
-		}
-		log.Info().
-			Str("func", "handleAuthKey").
-			Str("machine", machine.Name).
-			Str("ips", strings.Join(ips.ToStringSlice(), ",")).
-			Msgf("Assigning %s to %s", strings.Join(ips.ToStringSlice(), ","), machine.Name)
-
-		machine.Expiry = &registerRequest.Expiry
-		machine.AuthKeyID = uint(pak.ID)
-		machine.IPAddresses = ips
-		machine.NamespaceID = pak.NamespaceID
-
-		machine.NodeKey = NodePublicKeyStripPrefix(registerRequest.NodeKey)
-		// we update it just in case
-		machine.Registered = true
-		machine.RegisterMethod = RegisterMethodAuthKey
-		h.db.Save(&machine)
-
-		h.ipAllocationMutex.Unlock()
+	machineToRegister := Machine{
+		Name:           registerRequest.Hostinfo.Hostname,
+		NamespaceID:    pak.Namespace.ID,
+		MachineKey:     machineKeyStr,
+		RegisterMethod: RegisterMethodAuthKey,
+		Expiry:         &registerRequest.Expiry,
+		NodeKey:        nodeKey,
+		LastSeen:       &now,
+		AuthKeyID:      uint(pak.ID),
 	}

-	pak.Used = true
-	h.db.Save(&pak)
+	machine, err := h.RegisterMachine(
+		machineToRegister,
+	)
+	if err != nil {
+		log.Error().
+			Caller().
+			Err(err).
+			Msg("could not register machine")
+		machineRegistrations.WithLabelValues("new", RegisterMethodAuthKey, "error", pak.Namespace.Name).
+			Inc()
+		ctx.String(
+			http.StatusInternalServerError,
+			"could not register machine",
+		)
+
+		return
+	}
+
+	h.UsePreAuthKey(pak)

 	resp.MachineAuthorized = true
 	resp.User = *pak.Namespace.toUser()
@ -619,21 +608,21 @@ func (h *Headscale) handleAuthKey(
 		log.Error().
 			Caller().
 			Str("func", "handleAuthKey").
-			Str("machine", machine.Name).
+			Str("machine", registerRequest.Hostinfo.Hostname).
 			Err(err).
 			Msg("Cannot encode message")
-		machineRegistrations.WithLabelValues("new", "authkey", "error", machine.Namespace.Name).
+		machineRegistrations.WithLabelValues("new", RegisterMethodAuthKey, "error", pak.Namespace.Name).
 			Inc()
 		ctx.String(http.StatusInternalServerError, "Extremely sad!")

 		return
 	}
-	machineRegistrations.WithLabelValues("new", "authkey", "success", machine.Namespace.Name).
+	machineRegistrations.WithLabelValues("new", RegisterMethodAuthKey, "success", pak.Namespace.Name).
 		Inc()
 	ctx.Data(http.StatusOK, "application/json; charset=utf-8", respBody)
 	log.Info().
 		Str("func", "handleAuthKey").
-		Str("machine", machine.Name).
+		Str("machine", registerRequest.Hostinfo.Hostname).
 		Str("ips", strings.Join(machine.IPAddresses.ToStringSlice(), ", ")).
 		Msg("Successfully authenticated via AuthKey")
 }
--- a/app.go
+++ b/app.go
@ -55,8 +55,8 @@ const (
 	HTTPReadTimeout    = 30 * time.Second
 	privateKeyFileMode = 0o600

-	requestedExpiryCacheExpiration      = time.Minute * 5
-	requestedExpiryCacheCleanupInterval = time.Minute * 10
+	registerCacheExpiration = time.Minute * 15
+	registerCacheCleanup    = time.Minute * 20

 	errUnsupportedDatabase                 = Error("unsupported DB")
 	errUnsupportedLetsEncryptChallengeType = Error(
@ -148,11 +148,10 @@ type Headscale struct {

 	lastStateChange sync.Map

-	oidcProvider   *oidc.Provider
-	oauth2Config   *oauth2.Config
-	oidcStateCache *cache.Cache
+	oidcProvider *oidc.Provider
+	oauth2Config *oauth2.Config

-	requestedExpiryCache *cache.Cache
+	registrationCache *cache.Cache

 	ipAllocationMutex sync.Mutex
 }
@ -202,18 +201,18 @@ func NewHeadscale(cfg Config) (*Headscale, error) {
 		return nil, errUnsupportedDatabase
 	}

-	requestedExpiryCache := cache.New(
-		requestedExpiryCacheExpiration,
-		requestedExpiryCacheCleanupInterval,
+	registrationCache := cache.New(
+		registerCacheExpiration,
+		registerCacheCleanup,
 	)

 	app := Headscale{
-		cfg:                  cfg,
-		dbType:               cfg.DBtype,
-		dbString:             dbString,
-		privateKey:           privKey,
-		aclRules:             tailcfg.FilterAllowAll, // default allowall
-		requestedExpiryCache: requestedExpiryCache,
+		cfg:               cfg,
+		dbType:            cfg.DBtype,
+		dbString:          dbString,
+		privateKey:        privKey,
+		aclRules:          tailcfg.FilterAllowAll, // default allowall
+		registrationCache: registrationCache,
 	}

 	err = app.initDB()
--- a/app_test.go
+++ b/app_test.go
@ -5,7 +5,6 @@ import (
 	"os"
 	"testing"

-	"github.com/patrickmn/go-cache"
 	"gopkg.in/check.v1"
 	"inet.af/netaddr"
 )
@ -50,10 +49,6 @@ func (s *Suite) ResetDB(c *check.C) {
 		cfg:      cfg,
 		dbType:   "sqlite3",
 		dbString: tmpDir + "/headscale_test.db",
-		requestedExpiryCache: cache.New(
-			requestedExpiryCacheExpiration,
-			requestedExpiryCacheCleanupInterval,
-		),
 	}
 	err = app.initDB()
 	if err != nil {
--- a/cli_test.go
+++ b/cli_test.go
@ -1,38 +0,0 @@
-package headscale
-
-import (
-	"time"
-
-	"gopkg.in/check.v1"
-	"inet.af/netaddr"
-)
-
-func (s *Suite) TestRegisterMachine(c *check.C) {
-	namespace, err := app.CreateNamespace("test")
-	c.Assert(err, check.IsNil)
-
-	now := time.Now().UTC()
-
-	machine := Machine{
-		ID:          0,
-		MachineKey:  "8ce002a935f8c394e55e78fbbb410576575ff8ec5cfa2e627e4b807f1be15b0e",
-		NodeKey:     "bar",
-		DiscoKey:    "faa",
-		Name:        "testmachine",
-		NamespaceID: namespace.ID,
-		IPAddresses: []netaddr.IP{netaddr.MustParseIP("10.0.0.1")},
-		Expiry:      &now,
-	}
-	err = app.db.Save(&machine).Error
-	c.Assert(err, check.IsNil)
-
-	_, err = app.GetMachine(namespace.Name, machine.Name)
-	c.Assert(err, check.IsNil)
-
-	machineAfterRegistering, err := app.RegisterMachine(
-		machine.MachineKey,
-		namespace.Name,
-	)
-	c.Assert(err, check.IsNil)
-	c.Assert(machineAfterRegistering.Registered, check.Equals, true)
-}
--- a/db.go
+++ b/db.go
@ -8,6 +8,7 @@ import (
 	"time"

 	"github.com/glebarez/sqlite"
+	"github.com/rs/zerolog/log"
 	"gorm.io/driver/postgres"
 	"gorm.io/gorm"
 	"gorm.io/gorm/logger"
@ -39,6 +40,38 @@ func (h *Headscale) initDB() error {

 	_ = db.Migrator().RenameColumn(&Machine{}, "ip_address", "ip_addresses")

+	// If the Machine table has a column for registered,
+	// find all occourences of "false" and drop them. Then
+	// remove the column.
+	if db.Migrator().HasColumn(&Machine{}, "registered") {
+		log.Info().
+			Msg(`Database has legacy "registered" column in machine, removing...`)
+
+		machines := Machines{}
+		if err := h.db.Not("registered").Find(&machines).Error; err != nil {
+			log.Error().Err(err).Msg("Error accessing db")
+		}
+
+		for _, machine := range machines {
+			log.Info().
+				Str("machine", machine.Name).
+				Str("machine_key", machine.MachineKey).
+				Msg("Deleting unregistered machine")
+			if err := h.db.Delete(&Machine{}, machine.ID).Error; err != nil {
+				log.Error().
+					Err(err).
+					Str("machine", machine.Name).
+					Str("machine_key", machine.MachineKey).
+					Msg("Error deleting unregistered machine")
+			}
+		}
+
+		err := db.Migrator().DropColumn(&Machine{}, "registered")
+		if err != nil {
+			log.Error().Err(err).Msg("Error dropping registered column")
+		}
+	}
+
 	err = db.AutoMigrate(&Machine{})
 	if err != nil {
 		return err
--- a/dns_test.go
+++ b/dns_test.go
@ -164,7 +164,6 @@ func (s *Suite) TestDNSConfigMapResponseWithMagicDNS(c *check.C) {
 		Name:           "test_get_shared_nodes_1",
 		NamespaceID:    namespaceShared1.ID,
 		Namespace:      *namespaceShared1,
-		Registered:     true,
 		RegisterMethod: RegisterMethodAuthKey,
 		IPAddresses:    []netaddr.IP{netaddr.MustParseIP("100.64.0.1")},
 		AuthKeyID:      uint(preAuthKeyInShared1.ID),
@ -182,7 +181,6 @@ func (s *Suite) TestDNSConfigMapResponseWithMagicDNS(c *check.C) {
 		Name:           "test_get_shared_nodes_2",
 		NamespaceID:    namespaceShared2.ID,
 		Namespace:      *namespaceShared2,
-		Registered:     true,
 		RegisterMethod: RegisterMethodAuthKey,
 		IPAddresses:    []netaddr.IP{netaddr.MustParseIP("100.64.0.2")},
 		AuthKeyID:      uint(preAuthKeyInShared2.ID),
@ -200,7 +198,6 @@ func (s *Suite) TestDNSConfigMapResponseWithMagicDNS(c *check.C) {
 		Name:           "test_get_shared_nodes_3",
 		NamespaceID:    namespaceShared3.ID,
 		Namespace:      *namespaceShared3,
-		Registered:     true,
 		RegisterMethod: RegisterMethodAuthKey,
 		IPAddresses:    []netaddr.IP{netaddr.MustParseIP("100.64.0.3")},
 		AuthKeyID:      uint(preAuthKeyInShared3.ID),
@ -218,7 +215,6 @@ func (s *Suite) TestDNSConfigMapResponseWithMagicDNS(c *check.C) {
 		Name:           "test_get_shared_nodes_4",
 		NamespaceID:    namespaceShared1.ID,
 		Namespace:      *namespaceShared1,
-		Registered:     true,
 		RegisterMethod: RegisterMethodAuthKey,
 		IPAddresses:    []netaddr.IP{netaddr.MustParseIP("100.64.0.4")},
 		AuthKeyID:      uint(PreAuthKey2InShared1.ID),
@ -311,7 +307,6 @@ func (s *Suite) TestDNSConfigMapResponseWithoutMagicDNS(c *check.C) {
 		Name:           "test_get_shared_nodes_1",
 		NamespaceID:    namespaceShared1.ID,
 		Namespace:      *namespaceShared1,
-		Registered:     true,
 		RegisterMethod: RegisterMethodAuthKey,
 		IPAddresses:    []netaddr.IP{netaddr.MustParseIP("100.64.0.1")},
 		AuthKeyID:      uint(preAuthKeyInShared1.ID),
@ -329,7 +324,6 @@ func (s *Suite) TestDNSConfigMapResponseWithoutMagicDNS(c *check.C) {
 		Name:           "test_get_shared_nodes_2",
 		NamespaceID:    namespaceShared2.ID,
 		Namespace:      *namespaceShared2,
-		Registered:     true,
 		RegisterMethod: RegisterMethodAuthKey,
 		IPAddresses:    []netaddr.IP{netaddr.MustParseIP("100.64.0.2")},
 		AuthKeyID:      uint(preAuthKeyInShared2.ID),
@ -347,7 +341,6 @@ func (s *Suite) TestDNSConfigMapResponseWithoutMagicDNS(c *check.C) {
 		Name:           "test_get_shared_nodes_3",
 		NamespaceID:    namespaceShared3.ID,
 		Namespace:      *namespaceShared3,
-		Registered:     true,
 		RegisterMethod: RegisterMethodAuthKey,
 		IPAddresses:    []netaddr.IP{netaddr.MustParseIP("100.64.0.3")},
 		AuthKeyID:      uint(preAuthKeyInShared3.ID),
@ -365,7 +358,6 @@ func (s *Suite) TestDNSConfigMapResponseWithoutMagicDNS(c *check.C) {
 		Name:           "test_get_shared_nodes_4",
 		NamespaceID:    namespaceShared1.ID,
 		Namespace:      *namespaceShared1,
-		Registered:     true,
 		RegisterMethod: RegisterMethodAuthKey,
 		IPAddresses:    []netaddr.IP{netaddr.MustParseIP("100.64.0.4")},
 		AuthKeyID:      uint(preAuthKey2InShared1.ID),
--- a/gen/go/headscale/v1/machine.pb.go
+++ b/gen/go/headscale/v1/machine.pb.go
@ -85,13 +85,12 @@ type Machine struct {
 	IpAddresses          []string               `protobuf:"bytes,5,rep,name=ip_addresses,json=ipAddresses,proto3" json:"ip_addresses,omitempty"`
 	Name                 string                 `protobuf:"bytes,6,opt,name=name,proto3" json:"name,omitempty"`
 	Namespace            *Namespace             `protobuf:"bytes,7,opt,name=namespace,proto3" json:"namespace,omitempty"`
-	Registered           bool                   `protobuf:"varint,8,opt,name=registered,proto3" json:"registered,omitempty"`
-	RegisterMethod       RegisterMethod         `protobuf:"varint,9,opt,name=register_method,json=registerMethod,proto3,enum=headscale.v1.RegisterMethod" json:"register_method,omitempty"`
-	LastSeen             *timestamppb.Timestamp `protobuf:"bytes,10,opt,name=last_seen,json=lastSeen,proto3" json:"last_seen,omitempty"`
-	LastSuccessfulUpdate *timestamppb.Timestamp `protobuf:"bytes,11,opt,name=last_successful_update,json=lastSuccessfulUpdate,proto3" json:"last_successful_update,omitempty"`
-	Expiry               *timestamppb.Timestamp `protobuf:"bytes,12,opt,name=expiry,proto3" json:"expiry,omitempty"`
-	PreAuthKey           *PreAuthKey            `protobuf:"bytes,13,opt,name=pre_auth_key,json=preAuthKey,proto3" json:"pre_auth_key,omitempty"`
-	CreatedAt            *timestamppb.Timestamp `protobuf:"bytes,14,opt,name=created_at,json=createdAt,proto3" json:"created_at,omitempty"`
+	LastSeen             *timestamppb.Timestamp `protobuf:"bytes,8,opt,name=last_seen,json=lastSeen,proto3" json:"last_seen,omitempty"`
+	LastSuccessfulUpdate *timestamppb.Timestamp `protobuf:"bytes,9,opt,name=last_successful_update,json=lastSuccessfulUpdate,proto3" json:"last_successful_update,omitempty"`
+	Expiry               *timestamppb.Timestamp `protobuf:"bytes,10,opt,name=expiry,proto3" json:"expiry,omitempty"`
+	PreAuthKey           *PreAuthKey            `protobuf:"bytes,11,opt,name=pre_auth_key,json=preAuthKey,proto3" json:"pre_auth_key,omitempty"`
+	CreatedAt            *timestamppb.Timestamp `protobuf:"bytes,12,opt,name=created_at,json=createdAt,proto3" json:"created_at,omitempty"`
+	RegisterMethod       RegisterMethod         `protobuf:"varint,13,opt,name=register_method,json=registerMethod,proto3,enum=headscale.v1.RegisterMethod" json:"register_method,omitempty"`
 }

 func (x *Machine) Reset() {
@ -175,20 +174,6 @@ func (x *Machine) GetNamespace() *Namespace {
 	return nil
 }

-func (x *Machine) GetRegistered() bool {
-	if x != nil {
-		return x.Registered
-	}
-	return false
-}
-
-func (x *Machine) GetRegisterMethod() RegisterMethod {
-	if x != nil {
-		return x.RegisterMethod
-	}
-	return RegisterMethod_REGISTER_METHOD_UNSPECIFIED
-}
-
 func (x *Machine) GetLastSeen() *timestamppb.Timestamp {
 	if x != nil {
 		return x.LastSeen
@ -224,6 +209,13 @@ func (x *Machine) GetCreatedAt() *timestamppb.Timestamp {
 	return nil
 }

+func (x *Machine) GetRegisterMethod() RegisterMethod {
+	if x != nil {
+		return x.RegisterMethod
+	}
+	return RegisterMethod_REGISTER_METHOD_UNSPECIFIED
+}
+
 type RegisterMachineRequest struct {
 	state         protoimpl.MessageState
 	sizeCache     protoimpl.SizeCache
@ -822,7 +814,7 @@ var file_headscale_v1_machine_proto_rawDesc = []byte{
 	0x64, 0x73, 0x63, 0x61, 0x6c, 0x65, 0x2f, 0x76, 0x31, 0x2f, 0x6e, 0x61, 0x6d, 0x65, 0x73, 0x70,
 	0x61, 0x63, 0x65, 0x2e, 0x70, 0x72, 0x6f, 0x74, 0x6f, 0x1a, 0x1d, 0x68, 0x65, 0x61, 0x64, 0x73,
 	0x63, 0x61, 0x6c, 0x65, 0x2f, 0x76, 0x31, 0x2f, 0x70, 0x72, 0x65, 0x61, 0x75, 0x74, 0x68, 0x6b,
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@ -836,33 +828,31 @@ var file_headscale_v1_machine_proto_rawDesc = []byte{
 	0x6e, 0x61, 0x6d, 0x65, 0x12, 0x35, 0x0a, 0x09, 0x6e, 0x61, 0x6d, 0x65, 0x73, 0x70, 0x61, 0x63,
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@ -962,12 +952,12 @@ var file_headscale_v1_machine_proto_goTypes = []interface{}{
 }
 var file_headscale_v1_machine_proto_depIdxs = []int32{
 	14, // 0: headscale.v1.Machine.namespace:type_name -> headscale.v1.Namespace
-	0,  // 1: headscale.v1.Machine.register_method:type_name -> headscale.v1.RegisterMethod
-	15, // 2: headscale.v1.Machine.last_seen:type_name -> google.protobuf.Timestamp
-	15, // 3: headscale.v1.Machine.last_successful_update:type_name -> google.protobuf.Timestamp
-	15, // 4: headscale.v1.Machine.expiry:type_name -> google.protobuf.Timestamp
-	16, // 5: headscale.v1.Machine.pre_auth_key:type_name -> headscale.v1.PreAuthKey
-	15, // 6: headscale.v1.Machine.created_at:type_name -> google.protobuf.Timestamp
+	15, // 1: headscale.v1.Machine.last_seen:type_name -> google.protobuf.Timestamp
+	15, // 2: headscale.v1.Machine.last_successful_update:type_name -> google.protobuf.Timestamp
+	15, // 3: headscale.v1.Machine.expiry:type_name -> google.protobuf.Timestamp
+	16, // 4: headscale.v1.Machine.pre_auth_key:type_name -> headscale.v1.PreAuthKey
+	15, // 5: headscale.v1.Machine.created_at:type_name -> google.protobuf.Timestamp
+	0,  // 6: headscale.v1.Machine.register_method:type_name -> headscale.v1.RegisterMethod
 	1,  // 7: headscale.v1.RegisterMachineResponse.machine:type_name -> headscale.v1.Machine
 	1,  // 8: headscale.v1.GetMachineResponse.machine:type_name -> headscale.v1.Machine
 	1,  // 9: headscale.v1.ExpireMachineResponse.machine:type_name -> headscale.v1.Machine
--- a/gen/openapiv2/headscale/v1/headscale.swagger.json
+++ b/gen/openapiv2/headscale/v1/headscale.swagger.json
@ -885,12 +885,6 @@
        "namespace": {
          "$ref": "#/definitions/v1Namespace"
        },
-        "registered": {
-          "type": "boolean"
-        },
-        "registerMethod": {
-          "$ref": "#/definitions/v1RegisterMethod"
-        },
        "lastSeen": {
          "type": "string",
          "format": "date-time"
@ -909,6 +903,9 @@
        "createdAt": {
          "type": "string",
          "format": "date-time"
+        },
+        "registerMethod": {
+          "$ref": "#/definitions/v1RegisterMethod"
        }
      }
    },
--- a/grpcv1.go
+++ b/grpcv1.go
@ -157,9 +157,11 @@ func (api headscaleV1APIServer) RegisterMachine(
 		Str("namespace", request.GetNamespace()).
 		Str("machine_key", request.GetKey()).
 		Msg("Registering machine")
-	machine, err := api.h.RegisterMachine(
+
+	machine, err := api.h.RegisterMachineFromAuthCallback(
 		request.GetKey(),
 		request.GetNamespace(),
+		RegisterMethodCLI,
 	)
 	if err != nil {
 		return nil, err
@ -379,11 +381,11 @@ func (api headscaleV1APIServer) DebugCreateMachine(
 		HostInfo: HostInfo(hostinfo),
 	}

-	// log.Trace().Caller().Interface("machine", newMachine).Msg("")
-
-	if err := api.h.db.Create(&newMachine).Error; err != nil {
-		return nil, err
-	}
+	api.h.registrationCache.Set(
+		request.GetKey(),
+		newMachine,
+		registerCacheExpiration,
+	)

 	return &v1.DebugCreateMachineResponse{Machine: newMachine.toProto()}, nil
 }
--- a/integration_cli_test.go
+++ b/integration_cli_test.go
@ -621,12 +621,6 @@ func (s *IntegrationCLITestSuite) TestNodeCommand() {
 	assert.Equal(s.T(), "machine-4", listAll[3].Name)
 	assert.Equal(s.T(), "machine-5", listAll[4].Name)

-	assert.True(s.T(), listAll[0].Registered)
-	assert.True(s.T(), listAll[1].Registered)
-	assert.True(s.T(), listAll[2].Registered)
-	assert.True(s.T(), listAll[3].Registered)
-	assert.True(s.T(), listAll[4].Registered)
-
 	otherNamespaceMachineKeys := []string{
 		"b5b444774186d4217adcec407563a1223929465ee2c68a4da13af0d0185b4f8e",
 		"dc721977ac7415aafa87f7d4574cbe07c6b171834a6d37375782bdc1fb6b3584",
@ -710,9 +704,6 @@ func (s *IntegrationCLITestSuite) TestNodeCommand() {
 	assert.Equal(s.T(), "otherNamespace-machine-1", listAllWithotherNamespace[5].Name)
 	assert.Equal(s.T(), "otherNamespace-machine-2", listAllWithotherNamespace[6].Name)

-	assert.True(s.T(), listAllWithotherNamespace[5].Registered)
-	assert.True(s.T(), listAllWithotherNamespace[6].Registered)
-
 	// Test list all nodes after added otherNamespace
 	listOnlyotherNamespaceMachineNamespaceResult, err := ExecuteCommand(
 		&s.headscale,
@ -752,9 +743,6 @@ func (s *IntegrationCLITestSuite) TestNodeCommand() {
 		listOnlyotherNamespaceMachineNamespace[1].Name,
 	)

-	assert.True(s.T(), listOnlyotherNamespaceMachineNamespace[0].Registered)
-	assert.True(s.T(), listOnlyotherNamespaceMachineNamespace[1].Registered)
-
 	// Delete a machines
 	_, err = ExecuteCommand(
 		&s.headscale,
@ -979,7 +967,6 @@ func (s *IntegrationCLITestSuite) TestRouteCommand() {

 	assert.Equal(s.T(), uint64(1), machine.Id)
 	assert.Equal(s.T(), "route-machine", machine.Name)
-	assert.True(s.T(), machine.Registered)

 	listAllResult, err := ExecuteCommand(
 		&s.headscale,
--- a/machine.go
+++ b/machine.go
@ -18,11 +18,14 @@ import (
 )

 const (
-	errMachineNotFound            = Error("machine not found")
-	errMachineAlreadyRegistered   = Error("machine already registered")
-	errMachineRouteIsNotAvailable = Error("route is not available on machine")
-	errMachineAddressesInvalid    = Error("failed to parse machine addresses")
-	errHostnameTooLong            = Error("Hostname too long")
+	errMachineNotFound                  = Error("machine not found")
+	errMachineRouteIsNotAvailable       = Error("route is not available on machine")
+	errMachineAddressesInvalid          = Error("failed to parse machine addresses")
+	errMachineNotFoundRegistrationCache = Error(
+		"machine not found in registration cache",
+	)
+	errCouldNotConvertMachineInterface = Error("failed to convert machine interface")
+	errHostnameTooLong                 = Error("Hostname too long")
 )

 const (
@ -40,10 +43,11 @@ type Machine struct {
 	NamespaceID uint
 	Namespace   Namespace `gorm:"foreignKey:NamespaceID"`

-	Registered     bool // temp
 	RegisterMethod string
-	AuthKeyID      uint
-	AuthKey        *PreAuthKey
+
+	// TODO(kradalby): This seems like irrelevant information?
+	AuthKeyID uint
+	AuthKey   *PreAuthKey

 	LastSeen             *time.Time
 	LastSuccessfulUpdate *time.Time
@ -63,11 +67,6 @@ type (
 	MachinesP []*Machine
 )

-// For the time being this method is rather naive.
-func (machine Machine) isRegistered() bool {
-	return machine.Registered
-}
-
 type MachineAddresses []netaddr.IP

 func (ma MachineAddresses) ToStringSlice() []string {
@ -114,7 +113,7 @@ func (machine Machine) isExpired() bool {
 	// If Expiry is not set, the client has not indicated that
 	// it wants an expiry time, it is therefor considered
 	// to mean "not expired"
-	if machine.Expiry.IsZero() {
+	if machine.Expiry == nil || machine.Expiry.IsZero() {
 		return false
 	}

@ -171,6 +170,12 @@ func getFilteredByACLPeers(
 				machine.IPAddresses.ToStringSlice(),
 				peer.IPAddresses.ToStringSlice(),
 			) || // match source and destination
+				matchSourceAndDestinationWithRule(
+					rule.SrcIPs,
+					dst,
+					peer.IPAddresses.ToStringSlice(),
+					machine.IPAddresses.ToStringSlice(),
+				) || // match return path
 				matchSourceAndDestinationWithRule(
 					rule.SrcIPs,
 					dst,
@ -180,9 +185,21 @@ func getFilteredByACLPeers(
 				matchSourceAndDestinationWithRule(
 					rule.SrcIPs,
 					dst,
+					[]string{"*"},
+					[]string{"*"},
+				) || // match source and all destination
+				matchSourceAndDestinationWithRule(
+					rule.SrcIPs,
+					dst,
+					[]string{"*"},
 					peer.IPAddresses.ToStringSlice(),
+				) || // match source and all destination
+				matchSourceAndDestinationWithRule(
+					rule.SrcIPs,
+					dst,
+					[]string{"*"},
 					machine.IPAddresses.ToStringSlice(),
-				) { // match return path
+				) { // match all sources and source
 				peers[peer.ID] = peer
 			}
 		}
@ -212,7 +229,7 @@ func (h *Headscale) ListPeers(machine *Machine) (Machines, error) {
 		Msg("Finding direct peers")

 	machines := Machines{}
-	if err := h.db.Preload("AuthKey").Preload("AuthKey.Namespace").Preload("Namespace").Where("machine_key <> ? AND registered",
+	if err := h.db.Preload("AuthKey").Preload("AuthKey.Namespace").Preload("Namespace").Where("machine_key <> ?",
 		machine.MachineKey).Find(&machines).Error; err != nil {
 		log.Error().Err(err).Msg("Error accessing db")

@ -275,7 +292,7 @@ func (h *Headscale) getValidPeers(machine *Machine) (Machines, error) {
 	}

 	for _, peer := range peers {
-		if peer.isRegistered() && !peer.isExpired() {
+		if !peer.isExpired() {
 			validPeers = append(validPeers, peer)
 		}
 	}
@ -364,8 +381,6 @@ func (h *Headscale) RefreshMachine(machine *Machine, expiry time.Time) {

 // DeleteMachine softs deletes a Machine from the database.
 func (h *Headscale) DeleteMachine(machine *Machine) error {
-	machine.Registered = false
-	h.db.Save(&machine) // we mark it as unregistered, just in case
 	if err := h.db.Delete(&machine).Error; err != nil {
 		return err
 	}
@ -581,7 +596,7 @@ func (machine Machine) toNode(
 		LastSeen: machine.LastSeen,

 		KeepAlive:         true,
-		MachineAuthorized: machine.Registered,
+		MachineAuthorized: !machine.isExpired(),
 		Capabilities:      []string{tailcfg.CapabilityFileSharing},
 	}

@ -599,8 +614,6 @@ func (machine *Machine) toProto() *v1.Machine {
 		Name:        machine.Name,
 		Namespace:   machine.Namespace.toProto(),

-		Registered: machine.Registered,
-
 		// TODO(kradalby): Implement register method enum converter
 		// RegisterMethod: ,

@ -628,74 +641,50 @@ func (machine *Machine) toProto() *v1.Machine {
 	return machineProto
 }

-// RegisterMachine is executed from the CLI to register a new Machine using its MachineKey.
-func (h *Headscale) RegisterMachine(
+func (h *Headscale) RegisterMachineFromAuthCallback(
 	machineKeyStr string,
 	namespaceName string,
+	registrationMethod string,
 ) (*Machine, error) {
-	namespace, err := h.GetNamespace(namespaceName)
-	if err != nil {
-		return nil, err
-	}
+	if machineInterface, ok := h.registrationCache.Get(machineKeyStr); ok {
+		if registrationMachine, ok := machineInterface.(Machine); ok {
+			namespace, err := h.GetNamespace(namespaceName)
+			if err != nil {
+				return nil, fmt.Errorf(
+					"failed to find namespace in register machine from auth callback, %w",
+					err,
+				)
+			}

-	var machineKey key.MachinePublic
-	err = machineKey.UnmarshalText([]byte(MachinePublicKeyEnsurePrefix(machineKeyStr)))
-	if err != nil {
-		return nil, err
-	}
+			registrationMachine.NamespaceID = namespace.ID
+			registrationMachine.RegisterMethod = registrationMethod

-	log.Trace().
-		Caller().
-		Str("machine_key_str", machineKeyStr).
-		Str("machine_key", machineKey.String()).
-		Msg("Registering machine")
+			machine, err := h.RegisterMachine(
+				registrationMachine,
+			)

-	machine, err := h.GetMachineByMachineKey(machineKey)
-	if err != nil {
-		return nil, err
-	}
-
-	// TODO(kradalby): Currently, if it fails to find a requested expiry, non will be set
-	// This means that if a user is to slow with register a machine, it will possibly not
-	// have the correct expiry.
-	requestedTime := time.Time{}
-	if requestedTimeIf, found := h.requestedExpiryCache.Get(machineKey.String()); found {
-		log.Trace().
-			Caller().
-			Str("machine", machine.Name).
-			Msg("Expiry time found in cache, assigning to node")
-		if reqTime, ok := requestedTimeIf.(time.Time); ok {
-			requestedTime = reqTime
+			return machine, err
+		} else {
+			return nil, errCouldNotConvertMachineInterface
 		}
 	}

-	if machine.isRegistered() {
-		log.Trace().
-			Caller().
-			Str("machine", machine.Name).
-			Msg("machine already registered, reauthenticating")
+	return nil, errMachineNotFoundRegistrationCache
+}

-		h.RefreshMachine(machine, requestedTime)
-
-		return machine, nil
-	}
+// RegisterMachine is executed from the CLI to register a new Machine using its MachineKey.
+func (h *Headscale) RegisterMachine(machine Machine,
+) (*Machine, error) {
+	log.Trace().
+		Caller().
+		Str("machine_key", machine.MachineKey).
+		Msg("Registering machine")

 	log.Trace().
 		Caller().
 		Str("machine", machine.Name).
 		Msg("Attempting to register machine")

-	if machine.isRegistered() {
-		err := errMachineAlreadyRegistered
-		log.Error().
-			Caller().
-			Err(err).
-			Str("machine", machine.Name).
-			Msg("Attempting to register machine")
-
-		return nil, err
-	}
-
 	h.ipAllocationMutex.Lock()
 	defer h.ipAllocationMutex.Unlock()

@ -710,17 +699,8 @@ func (h *Headscale) RegisterMachine(
 		return nil, err
 	}

-	log.Trace().
-		Caller().
-		Str("machine", machine.Name).
-		Str("ip", strings.Join(ips.ToStringSlice(), ",")).
-		Msg("Found IP for host")
-
 	machine.IPAddresses = ips
-	machine.NamespaceID = namespace.ID
-	machine.Registered = true
-	machine.RegisterMethod = RegisterMethodCLI
-	machine.Expiry = &requestedTime
+
 	h.db.Save(&machine)

 	log.Trace().
@ -729,7 +709,7 @@ func (h *Headscale) RegisterMachine(
 		Str("ip", strings.Join(ips.ToStringSlice(), ",")).
 		Msg("Machine registered with the database")

-	return machine, nil
+	return &machine, nil
 }

 func (machine *Machine) GetAdvertisedRoutes() []netaddr.IPPrefix {
--- a/machine_test.go
+++ b/machine_test.go
@ -29,7 +29,6 @@ func (s *Suite) TestGetMachine(c *check.C) {
 		DiscoKey:       "faa",
 		Name:           "testmachine",
 		NamespaceID:    namespace.ID,
-		Registered:     true,
 		RegisterMethod: RegisterMethodAuthKey,
 		AuthKeyID:      uint(pak.ID),
 	}
@ -56,7 +55,6 @@ func (s *Suite) TestGetMachineByID(c *check.C) {
 		DiscoKey:       "faa",
 		Name:           "testmachine",
 		NamespaceID:    namespace.ID,
-		Registered:     true,
 		RegisterMethod: RegisterMethodAuthKey,
 		AuthKeyID:      uint(pak.ID),
 	}
@ -76,7 +74,6 @@ func (s *Suite) TestDeleteMachine(c *check.C) {
 		DiscoKey:       "faa",
 		Name:           "testmachine",
 		NamespaceID:    namespace.ID,
-		Registered:     true,
 		RegisterMethod: RegisterMethodAuthKey,
 		AuthKeyID:      uint(1),
 	}
@ -99,7 +96,6 @@ func (s *Suite) TestHardDeleteMachine(c *check.C) {
 		DiscoKey:       "faa",
 		Name:           "testmachine3",
 		NamespaceID:    namespace.ID,
-		Registered:     true,
 		RegisterMethod: RegisterMethodAuthKey,
 		AuthKeyID:      uint(1),
 	}
@ -130,7 +126,6 @@ func (s *Suite) TestListPeers(c *check.C) {
 			DiscoKey:       "faa" + strconv.Itoa(index),
 			Name:           "testmachine" + strconv.Itoa(index),
 			NamespaceID:    namespace.ID,
-			Registered:     true,
 			RegisterMethod: RegisterMethodAuthKey,
 			AuthKeyID:      uint(pak.ID),
 		}
@ -179,7 +174,6 @@ func (s *Suite) TestGetACLFilteredPeers(c *check.C) {
 			},
 			Name:           "testmachine" + strconv.Itoa(index),
 			NamespaceID:    stor[index%2].namespace.ID,
-			Registered:     true,
 			RegisterMethod: RegisterMethodAuthKey,
 			AuthKeyID:      uint(stor[index%2].key.ID),
 		}
@ -246,7 +240,6 @@ func (s *Suite) TestExpireMachine(c *check.C) {
 		DiscoKey:       "faa",
 		Name:           "testmachine",
 		NamespaceID:    namespace.ID,
-		Registered:     true,
 		RegisterMethod: RegisterMethodAuthKey,
 		AuthKeyID:      uint(pak.ID),
 		Expiry:         &time.Time{},
@ -284,6 +277,7 @@ func (s *Suite) TestSerdeAddressStrignSlice(c *check.C) {
 	}
 }

+// nolint
 func Test_getFilteredByACLPeers(t *testing.T) {
 	type args struct {
 		machines []Machine
@ -431,7 +425,7 @@ func Test_getFilteredByACLPeers(t *testing.T) {
 					},
 				},
 				machine: &Machine{ // current machine
-					ID:          1,
+					ID:          2,
 					IPAddresses: MachineAddresses{netaddr.MustParseIP("100.64.0.2")},
 					Namespace:   Namespace{Name: "marc"},
 				},
@ -444,6 +438,208 @@ func Test_getFilteredByACLPeers(t *testing.T) {
 				},
 			},
 		},
+		{
+			name: "rules allows all hosts to reach one destination",
+			args: args{
+				machines: []Machine{ // list of all machines in the database
+					{
+						ID: 1,
+						IPAddresses: MachineAddresses{
+							netaddr.MustParseIP("100.64.0.1"),
+						},
+						Namespace: Namespace{Name: "joe"},
+					},
+					{
+						ID: 2,
+						IPAddresses: MachineAddresses{
+							netaddr.MustParseIP("100.64.0.2"),
+						},
+						Namespace: Namespace{Name: "marc"},
+					},
+					{
+						ID: 3,
+						IPAddresses: MachineAddresses{
+							netaddr.MustParseIP("100.64.0.3"),
+						},
+						Namespace: Namespace{Name: "mickael"},
+					},
+				},
+				rules: []tailcfg.FilterRule{ // list of all ACLRules registered
+					{
+						SrcIPs: []string{"*"},
+						DstPorts: []tailcfg.NetPortRange{
+							{IP: "100.64.0.2"},
+						},
+					},
+				},
+				machine: &Machine{ // current machine
+					ID: 1,
+					IPAddresses: MachineAddresses{
+						netaddr.MustParseIP("100.64.0.1"),
+					},
+					Namespace: Namespace{Name: "joe"},
+				},
+			},
+			want: Machines{
+				{
+					ID: 2,
+					IPAddresses: MachineAddresses{
+						netaddr.MustParseIP("100.64.0.2"),
+					},
+					Namespace: Namespace{Name: "marc"},
+				},
+			},
+		},
+		{
+			name: "rules allows all hosts to reach one destination, destination can reach all hosts",
+			args: args{
+				machines: []Machine{ // list of all machines in the database
+					{
+						ID: 1,
+						IPAddresses: MachineAddresses{
+							netaddr.MustParseIP("100.64.0.1"),
+						},
+						Namespace: Namespace{Name: "joe"},
+					},
+					{
+						ID: 2,
+						IPAddresses: MachineAddresses{
+							netaddr.MustParseIP("100.64.0.2"),
+						},
+						Namespace: Namespace{Name: "marc"},
+					},
+					{
+						ID: 3,
+						IPAddresses: MachineAddresses{
+							netaddr.MustParseIP("100.64.0.3"),
+						},
+						Namespace: Namespace{Name: "mickael"},
+					},
+				},
+				rules: []tailcfg.FilterRule{ // list of all ACLRules registered
+					{
+						SrcIPs: []string{"*"},
+						DstPorts: []tailcfg.NetPortRange{
+							{IP: "100.64.0.2"},
+						},
+					},
+				},
+				machine: &Machine{ // current machine
+					ID: 2,
+					IPAddresses: MachineAddresses{
+						netaddr.MustParseIP("100.64.0.2"),
+					},
+					Namespace: Namespace{Name: "marc"},
+				},
+			},
+			want: Machines{
+				{
+					ID: 1,
+					IPAddresses: MachineAddresses{
+						netaddr.MustParseIP("100.64.0.1"),
+					},
+					Namespace: Namespace{Name: "joe"},
+				},
+				{
+					ID: 3,
+					IPAddresses: MachineAddresses{
+						netaddr.MustParseIP("100.64.0.3"),
+					},
+					Namespace: Namespace{Name: "mickael"},
+				},
+			},
+		},
+		{
+			name: "rule allows all hosts to reach all destinations",
+			args: args{
+				machines: []Machine{ // list of all machines in the database
+					{
+						ID: 1,
+						IPAddresses: MachineAddresses{
+							netaddr.MustParseIP("100.64.0.1"),
+						},
+						Namespace: Namespace{Name: "joe"},
+					},
+					{
+						ID: 2,
+						IPAddresses: MachineAddresses{
+							netaddr.MustParseIP("100.64.0.2"),
+						},
+						Namespace: Namespace{Name: "marc"},
+					},
+					{
+						ID: 3,
+						IPAddresses: MachineAddresses{
+							netaddr.MustParseIP("100.64.0.3"),
+						},
+						Namespace: Namespace{Name: "mickael"},
+					},
+				},
+				rules: []tailcfg.FilterRule{ // list of all ACLRules registered
+					{
+						SrcIPs: []string{"*"},
+						DstPorts: []tailcfg.NetPortRange{
+							{IP: "*"},
+						},
+					},
+				},
+				machine: &Machine{ // current machine
+					ID:          2,
+					IPAddresses: MachineAddresses{netaddr.MustParseIP("100.64.0.2")},
+					Namespace:   Namespace{Name: "marc"},
+				},
+			},
+			want: Machines{
+				{
+					ID: 1,
+					IPAddresses: MachineAddresses{
+						netaddr.MustParseIP("100.64.0.1"),
+					},
+					Namespace: Namespace{Name: "joe"},
+				},
+				{
+					ID:          3,
+					IPAddresses: MachineAddresses{netaddr.MustParseIP("100.64.0.3")},
+					Namespace:   Namespace{Name: "mickael"},
+				},
+			},
+		},
+		{
+			name: "without rule all communications are forbidden",
+			args: args{
+				machines: []Machine{ // list of all machines in the database
+					{
+						ID: 1,
+						IPAddresses: MachineAddresses{
+							netaddr.MustParseIP("100.64.0.1"),
+						},
+						Namespace: Namespace{Name: "joe"},
+					},
+					{
+						ID: 2,
+						IPAddresses: MachineAddresses{
+							netaddr.MustParseIP("100.64.0.2"),
+						},
+						Namespace: Namespace{Name: "marc"},
+					},
+					{
+						ID: 3,
+						IPAddresses: MachineAddresses{
+							netaddr.MustParseIP("100.64.0.3"),
+						},
+						Namespace: Namespace{Name: "mickael"},
+					},
+				},
+				rules: []tailcfg.FilterRule{ // list of all ACLRules registered
+				},
+				machine: &Machine{ // current machine
+					ID:          2,
+					IPAddresses: MachineAddresses{netaddr.MustParseIP("100.64.0.2")},
+					Namespace:   Namespace{Name: "marc"},
+				},
+			},
+			want: Machines{},
+		},
 	}
 	for _, tt := range tests {
 		t.Run(tt.name, func(t *testing.T) {
--- a/namespaces_test.go
+++ b/namespaces_test.go
@ -54,7 +54,6 @@ func (s *Suite) TestDestroyNamespaceErrors(c *check.C) {
 		DiscoKey:       "faa",
 		Name:           "testmachine",
 		NamespaceID:    namespace.ID,
-		Registered:     true,
 		RegisterMethod: RegisterMethodAuthKey,
 		AuthKeyID:      uint(pak.ID),
 	}
@ -146,7 +145,6 @@ func (s *Suite) TestGetMapResponseUserProfiles(c *check.C) {
 		Name:           "test_get_shared_nodes_1",
 		NamespaceID:    namespaceShared1.ID,
 		Namespace:      *namespaceShared1,
-		Registered:     true,
 		RegisterMethod: RegisterMethodAuthKey,
 		IPAddresses:    []netaddr.IP{netaddr.MustParseIP("100.64.0.1")},
 		AuthKeyID:      uint(preAuthKeyShared1.ID),
@ -164,7 +162,6 @@ func (s *Suite) TestGetMapResponseUserProfiles(c *check.C) {
 		Name:           "test_get_shared_nodes_2",
 		NamespaceID:    namespaceShared2.ID,
 		Namespace:      *namespaceShared2,
-		Registered:     true,
 		RegisterMethod: RegisterMethodAuthKey,
 		IPAddresses:    []netaddr.IP{netaddr.MustParseIP("100.64.0.2")},
 		AuthKeyID:      uint(preAuthKeyShared2.ID),
@ -182,7 +179,6 @@ func (s *Suite) TestGetMapResponseUserProfiles(c *check.C) {
 		Name:           "test_get_shared_nodes_3",
 		NamespaceID:    namespaceShared3.ID,
 		Namespace:      *namespaceShared3,
-		Registered:     true,
 		RegisterMethod: RegisterMethodAuthKey,
 		IPAddresses:    []netaddr.IP{netaddr.MustParseIP("100.64.0.3")},
 		AuthKeyID:      uint(preAuthKeyShared3.ID),
@ -200,7 +196,6 @@ func (s *Suite) TestGetMapResponseUserProfiles(c *check.C) {
 		Name:           "test_get_shared_nodes_4",
 		NamespaceID:    namespaceShared1.ID,
 		Namespace:      *namespaceShared1,
-		Registered:     true,
 		RegisterMethod: RegisterMethodAuthKey,
 		IPAddresses:    []netaddr.IP{netaddr.MustParseIP("100.64.0.4")},
 		AuthKeyID:      uint(preAuthKey2Shared1.ID),
--- a/oidc.go
+++ b/oidc.go
@ -10,21 +10,16 @@ import (
 	"html/template"
 	"net/http"
 	"strings"
-	"time"

 	"github.com/coreos/go-oidc/v3/oidc"
 	"github.com/gin-gonic/gin"
-	"github.com/patrickmn/go-cache"
 	"github.com/rs/zerolog/log"
 	"golang.org/x/oauth2"
-	"gorm.io/gorm"
 	"tailscale.com/types/key"
 )

 const (
-	oidcStateCacheExpiration      = time.Minute * 5
-	oidcStateCacheCleanupInterval = time.Minute * 10
-	randomByteSize                = 16
+	randomByteSize = 16
 )

 type IDTokenClaims struct {
@ -61,14 +56,6 @@ func (h *Headscale) initOIDC() error {
 		}
 	}

-	// init the state cache if it hasn't been already
-	if h.oidcStateCache == nil {
-		h.oidcStateCache = cache.New(
-			oidcStateCacheExpiration,
-			oidcStateCacheCleanupInterval,
-		)
-	}
-
 	return nil
 }

@ -101,7 +88,7 @@ func (h *Headscale) RegisterOIDC(ctx *gin.Context) {
 	stateStr := hex.EncodeToString(randomBlob)[:32]

 	// place the machine key into the state cache, so it can be retrieved later
-	h.oidcStateCache.Set(stateStr, machineKeyStr, oidcStateCacheExpiration)
+	h.registrationCache.Set(stateStr, machineKeyStr, registerCacheExpiration)

 	authURL := h.oauth2Config.AuthCodeURL(stateStr)
 	log.Debug().Msgf("Redirecting to %s for authentication", authURL)
@ -125,7 +112,6 @@ var oidcCallbackTemplate = template.Must(
 	</html>`),
 )

-// TODO: Why is the entire machine registration logic duplicated here?
 // OIDCCallback handles the callback from the OIDC endpoint
 // Retrieves the mkey from the state cache and adds the machine to the users email namespace
 // TODO: A confirmation page for new machines should be added to avoid phishing vulnerabilities
@ -197,7 +183,7 @@ func (h *Headscale) OIDCCallback(ctx *gin.Context) {
 	}

 	// retrieve machinekey from state cache
-	machineKeyIf, machineKeyFound := h.oidcStateCache.Get(state)
+	machineKeyIf, machineKeyFound := h.registrationCache.Get(state)

 	if !machineKeyFound {
 		log.Error().
@ -207,10 +193,12 @@ func (h *Headscale) OIDCCallback(ctx *gin.Context) {
 		return
 	}

-	machineKeyStr, machineKeyOK := machineKeyIf.(string)
+	machineKeyFromCache, machineKeyOK := machineKeyIf.(string)

 	var machineKey key.MachinePublic
-	err = machineKey.UnmarshalText([]byte(MachinePublicKeyEnsurePrefix(machineKeyStr)))
+	err = machineKey.UnmarshalText(
+		[]byte(MachinePublicKeyEnsurePrefix(machineKeyFromCache)),
+	)
 	if err != nil {
 		log.Error().
 			Msg("could not parse machine public key")
@ -229,33 +217,19 @@ func (h *Headscale) OIDCCallback(ctx *gin.Context) {
 		return
 	}

-	// TODO(kradalby): Currently, if it fails to find a requested expiry, non will be set
-	requestedTime := time.Time{}
-	if requestedTimeIf, found := h.requestedExpiryCache.Get(machineKey.String()); found {
-		if reqTime, ok := requestedTimeIf.(time.Time); ok {
-			requestedTime = reqTime
-		}
-	}
+	// retrieve machine information if it exist
+	// The error is not important, because if it does not
+	// exist, then this is a new machine and we will move
+	// on to registration.
+	machine, _ := h.GetMachineByMachineKey(machineKey)

-	// retrieve machine information
-	machine, err := h.GetMachineByMachineKey(machineKey)
-	if err != nil {
-		log.Error().Msg("machine key not found in database")
-		ctx.String(
-			http.StatusInternalServerError,
-			"could not get machine info from database",
-		)
-
-		return
-	}
-
-	if machine.isRegistered() {
+	if machine != nil {
 		log.Trace().
 			Caller().
 			Str("machine", machine.Name).
 			Msg("machine already registered, reauthenticating")

-		h.RefreshMachine(machine, requestedTime)
+		h.RefreshMachine(machine, *machine.Expiry)

 		var content bytes.Buffer
 		if err := oidcCallbackTemplate.Execute(&content, oidcCallbackTemplateConfig{
@ -279,8 +253,6 @@ func (h *Headscale) OIDCCallback(ctx *gin.Context) {
 		return
 	}

-	now := time.Now().UTC()
-
 	namespaceName, err := NormalizeNamespaceName(
 		claims.Email,
 		h.cfg.OIDC.StripEmaildomain,
@ -294,61 +266,58 @@ func (h *Headscale) OIDCCallback(ctx *gin.Context) {

 		return
 	}
+
 	// register the machine if it's new
-	if !machine.Registered {
-		log.Debug().Msg("Registering new machine after successful callback")
+	log.Debug().Msg("Registering new machine after successful callback")

-		namespace, err := h.GetNamespace(namespaceName)
-		if errors.Is(err, gorm.ErrRecordNotFound) {
-			namespace, err = h.CreateNamespace(namespaceName)
+	namespace, err := h.GetNamespace(namespaceName)
+	if errors.Is(err, errNamespaceNotFound) {
+		namespace, err = h.CreateNamespace(namespaceName)

-			if err != nil {
-				log.Error().
-					Err(err).
-					Caller().
-					Msgf("could not create new namespace '%s'", namespaceName)
-				ctx.String(
-					http.StatusInternalServerError,
-					"could not create new namespace",
-				)
-
-				return
-			}
-		} else if err != nil {
-			log.Error().
-				Caller().
-				Err(err).
-				Str("namespace", namespaceName).
-				Msg("could not find or create namespace")
-			ctx.String(
-				http.StatusInternalServerError,
-				"could not find or create namespace",
-			)
-
-			return
-		}
-
-		ips, err := h.getAvailableIPs()
 		if err != nil {
 			log.Error().
-				Caller().
 				Err(err).
-				Msg("could not get an IP from the pool")
+				Caller().
+				Msgf("could not create new namespace '%s'", namespaceName)
 			ctx.String(
 				http.StatusInternalServerError,
-				"could not get an IP from the pool",
+				"could not create new namespace",
 			)

 			return
 		}
+	} else if err != nil {
+		log.Error().
+			Caller().
+			Err(err).
+			Str("namespace", namespaceName).
+			Msg("could not find or create namespace")
+		ctx.String(
+			http.StatusInternalServerError,
+			"could not find or create namespace",
+		)

-		machine.IPAddresses = ips
-		machine.NamespaceID = namespace.ID
-		machine.Registered = true
-		machine.RegisterMethod = RegisterMethodOIDC
-		machine.LastSuccessfulUpdate = &now
-		machine.Expiry = &requestedTime
-		h.db.Save(&machine)
+		return
+	}
+
+	machineKeyStr := MachinePublicKeyStripPrefix(machineKey)
+
+	_, err = h.RegisterMachineFromAuthCallback(
+		machineKeyStr,
+		namespace.Name,
+		RegisterMethodOIDC,
+	)
+	if err != nil {
+		log.Error().
+			Caller().
+			Err(err).
+			Msg("could not register machine")
+		ctx.String(
+			http.StatusInternalServerError,
+			"could not register machine",
+		)
+
+		return
 	}

 	var content bytes.Buffer
--- a/preauth_keys.go
+++ b/preauth_keys.go
@ -113,6 +113,12 @@ func (h *Headscale) ExpirePreAuthKey(k *PreAuthKey) error {
 	return nil
 }

+// UsePreAuthKey marks a PreAuthKey as used.
+func (h *Headscale) UsePreAuthKey(k *PreAuthKey) {
+	k.Used = true
+	h.db.Save(k)
+}
+
 // checkKeyValidity does the heavy lifting for validation of the PreAuthKey coming from a node
 // If returns no error and a PreAuthKey, it can be used.
 func (h *Headscale) checkKeyValidity(k string) (*PreAuthKey, error) {
--- a/preauth_keys_test.go
+++ b/preauth_keys_test.go
@ -80,7 +80,6 @@ func (*Suite) TestAlreadyUsedKey(c *check.C) {
 		DiscoKey:       "faa",
 		Name:           "testest",
 		NamespaceID:    namespace.ID,
-		Registered:     true,
 		RegisterMethod: RegisterMethodAuthKey,
 		AuthKeyID:      uint(pak.ID),
 	}
@ -105,7 +104,6 @@ func (*Suite) TestReusableBeingUsedKey(c *check.C) {
 		DiscoKey:       "faa",
 		Name:           "testest",
 		NamespaceID:    namespace.ID,
-		Registered:     true,
 		RegisterMethod: RegisterMethodAuthKey,
 		AuthKeyID:      uint(pak.ID),
 	}
@ -143,7 +141,6 @@ func (*Suite) TestEphemeralKey(c *check.C) {
 		DiscoKey:       "faa",
 		Name:           "testest",
 		NamespaceID:    namespace.ID,
-		Registered:     true,
 		RegisterMethod: RegisterMethodAuthKey,
 		LastSeen:       &now,
 		AuthKeyID:      uint(pak.ID),
--- a/proto/headscale/v1/machine.proto
+++ b/proto/headscale/v1/machine.proto
@ -22,16 +22,16 @@ message Machine {
    string          name         = 6;
    Namespace namespace          = 7;

-    bool           registered      = 8;
-    RegisterMethod register_method = 9;

-    google.protobuf.Timestamp last_seen              = 10;
-    google.protobuf.Timestamp last_successful_update = 11;
-    google.protobuf.Timestamp expiry                 = 12;
+    google.protobuf.Timestamp last_seen              = 8;
+    google.protobuf.Timestamp last_successful_update = 9;
+    google.protobuf.Timestamp expiry                 = 10;

-    PreAuthKey pre_auth_key = 13;
+    PreAuthKey pre_auth_key = 11;

-    google.protobuf.Timestamp created_at = 14;
+    google.protobuf.Timestamp created_at = 12;
+
+    RegisterMethod register_method = 13;
    // google.protobuf.Timestamp updated_at = 14;
    // google.protobuf.Timestamp deleted_at = 15;

--- a/routes_test.go
+++ b/routes_test.go
@ -30,7 +30,6 @@ func (s *Suite) TestGetRoutes(c *check.C) {
 		DiscoKey:       "faa",
 		Name:           "test_get_route_machine",
 		NamespaceID:    namespace.ID,
-		Registered:     true,
 		RegisterMethod: RegisterMethodAuthKey,
 		AuthKeyID:      uint(pak.ID),
 		HostInfo:       HostInfo(hostInfo),
@ -82,7 +81,6 @@ func (s *Suite) TestGetEnableRoutes(c *check.C) {
 		DiscoKey:       "faa",
 		Name:           "test_enable_route_machine",
 		NamespaceID:    namespace.ID,
-		Registered:     true,
 		RegisterMethod: RegisterMethodAuthKey,
 		AuthKeyID:      uint(pak.ID),
 		HostInfo:       HostInfo(hostInfo),
--- a/utils_test.go
+++ b/utils_test.go
@ -36,7 +36,6 @@ func (s *Suite) TestGetUsedIps(c *check.C) {
 		DiscoKey:       "faa",
 		Name:           "testmachine",
 		NamespaceID:    namespace.ID,
-		Registered:     true,
 		RegisterMethod: RegisterMethodAuthKey,
 		AuthKeyID:      uint(pak.ID),
 		IPAddresses:    ips,
@ -85,7 +84,6 @@ func (s *Suite) TestGetMultiIp(c *check.C) {
 			DiscoKey:       "faa",
 			Name:           "testmachine",
 			NamespaceID:    namespace.ID,
-			Registered:     true,
 			RegisterMethod: RegisterMethodAuthKey,
 			AuthKeyID:      uint(pak.ID),
 			IPAddresses:    ips,
@ -176,7 +174,6 @@ func (s *Suite) TestGetAvailableIpMachineWithoutIP(c *check.C) {
 		DiscoKey:       "faa",
 		Name:           "testmachine",
 		NamespaceID:    namespace.ID,
-		Registered:     true,
 		RegisterMethod: RegisterMethodAuthKey,
 		AuthKeyID:      uint(pak.ID),
 	}