diff --git a/utils.go b/utils.go
index 7011e63d..d2b6b902 100644
--- a/utils.go
+++ b/utils.go
@@ -141,36 +141,32 @@ func (h *Headscale) getAvailableIP() (*netaddr.IP, error) {
 		return nil, err
 	}
 
+	ipPrefixNetworkAddress, ipPrefixBroadcastAddress := func() (netaddr.IP, netaddr.IP) {
+		ipRange := ipPrefix.Range()
+		return ipRange.From(), ipRange.To()
+	}()
+
 	// Get the first IP in our prefix
-	ip := ipPrefix.IP()
+	ip := ipPrefixNetworkAddress.Next()
 
 	for {
 		if !ipPrefix.Contains(ip) {
 			return nil, errCouldNotAllocateIP
 		}
 
-		// Some OS (including Linux) does not like when IPs ends with 0 or 255, which
-		// is typically called network or broadcast. Lets avoid them and continue
-		// to look when we get one of those traditionally reserved IPs.
-		ipRaw := ip.As4()
-		if ipRaw[3] == 0 || ipRaw[3] == 255 {
+		switch {
+		case ip.Compare(ipPrefixBroadcastAddress) == 0:
+			fallthrough
+		case containsIPs(usedIps, ip):
+			fallthrough
+		case ip.IsZero() || ip.IsLoopback():
 			ip = ip.Next()
 
 			continue
-		}
 
-		if ip.IsZero() &&
-			ip.IsLoopback() {
-			ip = ip.Next()
-
-			continue
-		}
-
-		if !containsIPs(usedIps, ip) {
+		default:
 			return &ip, nil
 		}
-
-		ip = ip.Next()
 	}
 }
 
diff --git a/utils_test.go b/utils_test.go
index 95722a83..9b0295b3 100644
--- a/utils_test.go
+++ b/utils_test.go
@@ -93,7 +93,7 @@ func (s *Suite) TestGetMultiIp(c *check.C) {
 
 	c.Assert(ips[0], check.Equals, netaddr.MustParseIP("10.27.0.1"))
 	c.Assert(ips[9], check.Equals, netaddr.MustParseIP("10.27.0.10"))
-	c.Assert(ips[300], check.Equals, netaddr.MustParseIP("10.27.1.47"))
+	c.Assert(ips[300], check.Equals, netaddr.MustParseIP("10.27.1.45"))
 
 	// Check that we can read back the IPs
 	machine1, err := app.GetMachineByID(1)
@@ -112,7 +112,7 @@ func (s *Suite) TestGetMultiIp(c *check.C) {
 		netaddr.MustParseIP("10.27.0.50").String(),
 	)
 
-	expectedNextIP := netaddr.MustParseIP("10.27.1.97")
+	expectedNextIP := netaddr.MustParseIP("10.27.1.95")
 	nextIP, err := app.getAvailableIP()
 	c.Assert(err, check.IsNil)