diff --git a/api.go b/api.go
index 50af5522..92186ee8 100644
--- a/api.go
+++ b/api.go
@@ -19,10 +19,13 @@ import (
 )
 
 const (
-	reservedResponseHeaderSize = 4
-	RegisterMethodAuthKey      = "authKey"
-	RegisterMethodOIDC         = "oidc"
-	RegisterMethodCLI          = "cli"
+	reservedResponseHeaderSize               = 4
+	RegisterMethodAuthKey                    = "authKey"
+	RegisterMethodOIDC                       = "oidc"
+	RegisterMethodCLI                        = "cli"
+	ErrRegisterMethodCLIDoesNotSupportExpire = Error(
+		"machines registered with CLI does not support expire",
+	)
 )
 
 // KeyHandler provides the Headscale pub key
@@ -441,7 +444,16 @@ func (h *Headscale) handleMachineRegistrationNew(
 	}
 
 	if !reqisterRequest.Expiry.IsZero() {
-		machine.Expiry = &reqisterRequest.Expiry
+		log.Trace().
+			Caller().
+			Str("machine", machine.Name).
+			Time("expiry", reqisterRequest.Expiry).
+			Msg("Non-zero expiry time requested, adding to cache")
+		h.requestedExpiryCache.Set(
+			idKey.HexString(),
+			reqisterRequest.Expiry,
+			requestedExpiryCacheExpiration,
+		)
 	}
 
 	machine.NodeKey = wgkey.Key(reqisterRequest.NodeKey).HexString() // save the NodeKey
diff --git a/app.go b/app.go
index b2b545b4..0d3332dd 100644
--- a/app.go
+++ b/app.go
@@ -53,6 +53,9 @@ const (
 	updateInterval  = 5000
 	HTTPReadTimeout = 30 * time.Second
 
+	requestedExpiryCacheExpiration      = time.Minute * 5
+	requestedExpiryCacheCleanupInterval = time.Minute * 10
+
 	errUnsupportedDatabase                 = Error("unsupported DB")
 	errUnsupportedLetsEncryptChallengeType = Error(
 		"unknown value for Lets Encrypt challenge type",
@@ -139,6 +142,8 @@ type Headscale struct {
 	oidcProvider   *oidc.Provider
 	oauth2Config   *oauth2.Config
 	oidcStateCache *cache.Cache
+
+	requestedExpiryCache *cache.Cache
 }
 
 // NewHeadscale returns the Headscale app.
@@ -171,13 +176,19 @@ func NewHeadscale(cfg Config) (*Headscale, error) {
 		return nil, errUnsupportedDatabase
 	}
 
+	requestedExpiryCache := cache.New(
+		requestedExpiryCacheExpiration,
+		requestedExpiryCacheCleanupInterval,
+	)
+
 	app := Headscale{
-		cfg:        cfg,
-		dbType:     cfg.DBtype,
-		dbString:   dbString,
-		privateKey: privKey,
-		publicKey:  &pubKey,
-		aclRules:   tailcfg.FilterAllowAll, // default allowall
+		cfg:                  cfg,
+		dbType:               cfg.DBtype,
+		dbString:             dbString,
+		privateKey:           privKey,
+		publicKey:            &pubKey,
+		aclRules:             tailcfg.FilterAllowAll, // default allowall
+		requestedExpiryCache: requestedExpiryCache,
 	}
 
 	err = app.initDB()
diff --git a/machine.go b/machine.go
index dd7124ec..06fec743 100644
--- a/machine.go
+++ b/machine.go
@@ -616,6 +616,31 @@ func (h *Headscale) RegisterMachine(
 		return nil, errMachineNotFound
 	}
 
+	// 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.HexString()); 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
+		}
+	}
+
+	if machine.isRegistered() {
+		log.Trace().
+			Caller().
+			Str("machine", machine.Name).
+			Msg("machine already registered, reauthenticating")
+
+		h.RefreshMachine(&machine, requestedTime)
+
+		return &machine, nil
+	}
+
 	log.Trace().
 		Caller().
 		Str("machine", machine.Name).
diff --git a/oidc.go b/oidc.go
index 2f7d6d61..9b0a3087 100644
--- a/oidc.go
+++ b/oidc.go
@@ -199,6 +199,14 @@ 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); found {
+		if reqTime, ok := requestedTimeIf.(time.Time); ok {
+			requestedTime = reqTime
+		}
+	}
+
 	// retrieve machine information
 	machine, err := h.GetMachineByMachineKey(machineKey)
 	if err != nil {