diff --git a/api/api.go b/api/api.go
index 047ce08..895140b 100644
--- a/api/api.go
+++ b/api/api.go
@@ -78,6 +78,13 @@ type MetadataChangeRequest struct {
 	Postures    map[string]any `json:"postures"`
 }
 
+// JITConnectionRequest defines the structure for a dynamic Just-In-Time connection request.
+// Either SiteID or ResourceID must be provided (but not necessarily both).
+type JITConnectionRequest struct {
+	Site     string `json:"site,omitempty"`
+	Resource string `json:"resource,omitempty"`
+}
+
 // API represents the HTTP server and its state
 type API struct {
 	addr       string
@@ -92,6 +99,7 @@ type API struct {
 	onExit           func() error
 	onRebind         func() error
 	onPowerMode      func(PowerModeRequest) error
+	onJITConnect     func(JITConnectionRequest) error
 
 	statusMu     sync.RWMutex
 	peerStatuses map[int]*PeerStatus
@@ -143,6 +151,7 @@ func (s *API) SetHandlers(
 	onExit func() error,
 	onRebind func() error,
 	onPowerMode func(PowerModeRequest) error,
+	onJITConnect func(JITConnectionRequest) error,
 ) {
 	s.onConnect = onConnect
 	s.onSwitchOrg = onSwitchOrg
@@ -151,6 +160,7 @@ func (s *API) SetHandlers(
 	s.onExit = onExit
 	s.onRebind = onRebind
 	s.onPowerMode = onPowerMode
+	s.onJITConnect = onJITConnect
 }
 
 // Start starts the HTTP server
@@ -169,6 +179,7 @@ func (s *API) Start() error {
 	mux.HandleFunc("/health", s.handleHealth)
 	mux.HandleFunc("/rebind", s.handleRebind)
 	mux.HandleFunc("/power-mode", s.handlePowerMode)
+	mux.HandleFunc("/jit-connect", s.handleJITConnect)
 
 	s.server = &http.Server{
 		Handler: mux,
@@ -633,6 +644,54 @@ func (s *API) handleRebind(w http.ResponseWriter, r *http.Request) {
 	})
 }
 
+// handleJITConnect handles the /jit-connect endpoint.
+// It initiates a dynamic Just-In-Time connection to a site identified by either
+// a site or a resource. Exactly one of the two must be provided.
+func (s *API) handleJITConnect(w http.ResponseWriter, r *http.Request) {
+	if r.Method != http.MethodPost {
+		http.Error(w, "Method not allowed", http.StatusMethodNotAllowed)
+		return
+	}
+
+	var req JITConnectionRequest
+	if err := json.NewDecoder(r.Body).Decode(&req); err != nil {
+		http.Error(w, fmt.Sprintf("Invalid request body: %v", err), http.StatusBadRequest)
+		return
+	}
+
+	// Validate that exactly one of site or resource is provided
+	if req.Site == "" && req.Resource == "" {
+		http.Error(w, "Missing required field: either site or resource must be provided", http.StatusBadRequest)
+		return
+	}
+	if req.Site != "" && req.Resource != "" {
+		http.Error(w, "Ambiguous request: provide either site or resource, not both", http.StatusBadRequest)
+		return
+	}
+
+	if req.Site != "" {
+		logger.Info("Received JIT connection request via API: site=%s", req.Site)
+	} else {
+		logger.Info("Received JIT connection request via API: resource=%s", req.Resource)
+	}
+
+	if s.onJITConnect != nil {
+		if err := s.onJITConnect(req); err != nil {
+			http.Error(w, fmt.Sprintf("JIT connection failed: %v", err), http.StatusInternalServerError)
+			return
+		}
+	} else {
+		http.Error(w, "JIT connect handler not configured", http.StatusNotImplemented)
+		return
+	}
+
+	w.Header().Set("Content-Type", "application/json")
+	w.WriteHeader(http.StatusAccepted)
+	_ = json.NewEncoder(w).Encode(map[string]string{
+		"status": "JIT connection request accepted",
+	})
+}
+
 // handlePowerMode handles the /power-mode endpoint
 // This allows changing the power mode between "normal" and "low"
 func (s *API) handlePowerMode(w http.ResponseWriter, r *http.Request) {
diff --git a/olm/data.go b/olm/data.go
index 8bd0997..015931b 100644
--- a/olm/data.go
+++ b/olm/data.go
@@ -220,6 +220,7 @@ func (o *Olm) handleSync(msg websocket.WSMessage) {
 			logger.Info("Sync: Adding new peer for site %d", siteId)
 
 			o.holePunchManager.TriggerHolePunch()
+			o.holePunchManager.ResetServerHolepunchInterval() // start sending immediately again so we fill in the endpoint on the cloud
 
 			// // TODO: do we need to send the message to the cloud to add the peer that way?
 			// if err := o.peerManager.AddPeer(expectedSite); err != nil {
diff --git a/olm/olm.go b/olm/olm.go
index 9bd41b2..fa32ebd 100644
--- a/olm/olm.go
+++ b/olm/olm.go
@@ -66,6 +66,7 @@ type Olm struct {
 	updateRegister func(newData any)
 
 	stopPeerSend func()
+	stopPeerInit func()
 
 	// WaitGroup to track tunnel lifecycle
 	tunnelWg sync.WaitGroup
@@ -284,6 +285,16 @@ func (o *Olm) registerAPICallbacks() {
 			logger.Info("Processing power mode change request via API: mode=%s", req.Mode)
 			return o.SetPowerMode(req.Mode)
 		},
+		func(req api.JITConnectionRequest) error {
+			logger.Info("Processing JIT connect request via API: site=%s resource=%s", req.Site, req.Resource)
+			
+			o.stopPeerInit, _ = o.websocket.SendMessageInterval("olm/wg/server/peer/init", map[string]interface{}{
+				"siteId": req.Site,
+				"resourceId": req.Resource,
+			}, 2*time.Second, 10)	
+			
+			return nil
+		},
 	)
 }