diff --git a/cmd/server/server.go b/cmd/server/server.go
index 56b07ea..3afe050 100644
--- a/cmd/server/server.go
+++ b/cmd/server/server.go
@@ -112,6 +112,7 @@ func runServer(ctx context.Context, logger *slog.Logger, argsToPass []string) er
 		ChatBasePath:   viper.GetString(FlagChatBasePath),
 		AllowedHosts:   viper.GetStringSlice(FlagAllowedHosts),
 		AllowedOrigins: viper.GetStringSlice(FlagAllowedOrigins),
+		InitialPrompt:  viper.GetString(FlagInitialPrompt),
 	})
 	if err != nil {
 		return xerrors.Errorf("failed to create server: %w", err)
@@ -174,6 +175,7 @@ const (
 	FlagAllowedHosts   = "allowed-hosts"
 	FlagAllowedOrigins = "allowed-origins"
 	FlagExit           = "exit"
+	FlagInitialPrompt  = "initial-prompt"
 )
 
 func CreateServerCmd() *cobra.Command {
@@ -211,6 +213,7 @@ func CreateServerCmd() *cobra.Command {
 		{FlagAllowedHosts, "a", []string{"localhost", "127.0.0.1", "[::1]"}, "HTTP allowed hosts (hostnames only, no ports). Use '*' for all, comma-separated list via flag, space-separated list via AGENTAPI_ALLOWED_HOSTS env var", "stringSlice"},
 		// localhost:3284 is the default origin when you open the chat interface in your browser. localhost:3000 and 3001 are used during development.
 		{FlagAllowedOrigins, "o", []string{"http://localhost:3284", "http://localhost:3000", "http://localhost:3001"}, "HTTP allowed origins. Use '*' for all, comma-separated list via flag, space-separated list via AGENTAPI_ALLOWED_ORIGINS env var", "stringSlice"},
+		{FlagInitialPrompt, "I", "", "Initial prompt for the agent (recommended only if the agent doesn't support initial prompt in interaction mode)", "string"},
 	}
 
 	for _, spec := range flagSpecs {
diff --git a/lib/httpapi/server.go b/lib/httpapi/server.go
index 08d92c4..11994f0 100644
--- a/lib/httpapi/server.go
+++ b/lib/httpapi/server.go
@@ -95,6 +95,7 @@ type ServerConfig struct {
 	ChatBasePath   string
 	AllowedHosts   []string
 	AllowedOrigins []string
+	InitialPrompt  string
 }
 
 // Validate allowed hosts don't contain whitespace, commas, schemes, or ports.
@@ -230,7 +231,7 @@ func NewServer(ctx context.Context, config ServerConfig) (*Server, error) {
 		SnapshotInterval:      snapshotInterval,
 		ScreenStabilityLength: 2 * time.Second,
 		FormatMessage:         formatMessage,
-	})
+	}, config.InitialPrompt)
 	emitter := NewEventEmitter(1024)
 	s := &Server{
 		router:       router,
@@ -306,7 +307,19 @@ func (s *Server) StartSnapshotLoop(ctx context.Context) {
 	s.conversation.StartSnapshotLoop(ctx)
 	go func() {
 		for {
-			s.emitter.UpdateStatusAndEmitChanges(s.conversation.Status())
+			currentStatus := s.conversation.Status()
+
+			// Send initial prompt when agent becomes stable for the first time
+			if !s.conversation.InitialPromptSent && convertStatus(currentStatus) == AgentStatusStable {
+				if err := s.conversation.SendMessage(FormatMessage(s.agentType, s.conversation.InitialPrompt)...); err != nil {
+					s.logger.Error("Failed to send initial prompt", "error", err)
+				} else {
+					s.conversation.InitialPromptSent = true
+					currentStatus = st.ConversationStatusChanging
+					s.logger.Info("Initial prompt sent successfully")
+				}
+			}
+			s.emitter.UpdateStatusAndEmitChanges(currentStatus)
 			s.emitter.UpdateMessagesAndEmitChanges(s.conversation.Messages())
 			s.emitter.UpdateScreenAndEmitChanges(s.conversation.Screen())
 			time.Sleep(snapshotInterval)
diff --git a/lib/screentracker/conversation.go b/lib/screentracker/conversation.go
index 7777e04..4617e8e 100644
--- a/lib/screentracker/conversation.go
+++ b/lib/screentracker/conversation.go
@@ -74,6 +74,10 @@ type Conversation struct {
 	messages                    []ConversationMessage
 	screenBeforeLastUserMessage string
 	lock                        sync.Mutex
+	// InitialPrompt is the initial prompt passed to the agent
+	InitialPrompt string
+	// InitialPromptSent keeps track if the InitialPrompt has been successfully sent to the agents
+	InitialPromptSent bool
 }
 
 type ConversationStatus string
@@ -94,7 +98,7 @@ func getStableSnapshotsThreshold(cfg ConversationConfig) int {
 	return threshold + 1
 }
 
-func NewConversation(ctx context.Context, cfg ConversationConfig) *Conversation {
+func NewConversation(ctx context.Context, cfg ConversationConfig, initialPrompt string) *Conversation {
 	threshold := getStableSnapshotsThreshold(cfg)
 	c := &Conversation{
 		cfg:                      cfg,
@@ -107,6 +111,8 @@ func NewConversation(ctx context.Context, cfg ConversationConfig) *Conversation
 				Time:    cfg.GetTime(),
 			},
 		},
+		InitialPrompt:     initialPrompt,
+		InitialPromptSent: len(initialPrompt) == 0,
 	}
 	return c
 }
diff --git a/lib/screentracker/conversation_test.go b/lib/screentracker/conversation_test.go
index 53c77fd..92fe5ac 100644
--- a/lib/screentracker/conversation_test.go
+++ b/lib/screentracker/conversation_test.go
@@ -42,7 +42,7 @@ func statusTest(t *testing.T, params statusTestParams) {
 		if params.cfg.GetTime == nil {
 			params.cfg.GetTime = func() time.Time { return time.Now() }
 		}
-		c := st.NewConversation(ctx, params.cfg)
+		c := st.NewConversation(ctx, params.cfg, "")
 		assert.Equal(t, st.ConversationStatusInitializing, c.Status())
 
 		for i, step := range params.steps {
@@ -147,7 +147,7 @@ func TestMessages(t *testing.T) {
 		for _, opt := range opts {
 			opt(&cfg)
 		}
-		return st.NewConversation(context.Background(), cfg)
+		return st.NewConversation(context.Background(), cfg, "")
 	}
 
 	t.Run("messages are copied", func(t *testing.T) {