diff --git a/client/SDL/SDL3/sdl_freerdp.cpp b/client/SDL/SDL3/sdl_freerdp.cpp
index aa6166d72..3be30a6bf 100644
--- a/client/SDL/SDL3/sdl_freerdp.cpp
+++ b/client/SDL/SDL3/sdl_freerdp.cpp
@@ -139,6 +139,7 @@ enum SDL_EXIT_CODE
 	SDL_EXIT_CONNECT_ACCOUNT_EXPIRED = 157,
 	SDL_EXIT_CONNECT_LOGON_TYPE_NOT_GRANTED = 158,
 	SDL_EXIT_CONNECT_NO_OR_MISSING_CREDENTIALS = 159,
+	SDL_EXIT_CONNECT_TARGET_BOOTING = 160,
 
 	SDL_EXIT_UNKNOWN = 255,
 };
@@ -188,6 +189,7 @@ static const struct sdl_exit_code_map_t sdl_exit_code_map[] = {
 	ENTRY(FREERDP_ERROR_AUTHENTICATION_FAILED, SDL_EXIT_AUTH_FAILURE),
 	ENTRY(FREERDP_ERROR_SECURITY_NEGO_CONNECT_FAILED, SDL_EXIT_NEGO_FAILURE),
 	ENTRY(FREERDP_ERROR_CONNECT_LOGON_FAILURE, SDL_EXIT_LOGON_FAILURE),
+	ENTRY(FREERDP_ERROR_CONNECT_TARGET_BOOTING, SDL_EXIT_CONNECT_TARGET_BOOTING),
 	ENTRY(FREERDP_ERROR_CONNECT_ACCOUNT_LOCKED_OUT, SDL_EXIT_ACCOUNT_LOCKED_OUT),
 	ENTRY(FREERDP_ERROR_PRE_CONNECT_FAILED, SDL_EXIT_PRE_CONNECT_FAILED),
 	ENTRY(FREERDP_ERROR_CONNECT_UNDEFINED, SDL_EXIT_CONNECT_UNDEFINED),
diff --git a/client/X11/xf_client.c b/client/X11/xf_client.c
index cd2f27eaa..854404e0e 100644
--- a/client/X11/xf_client.c
+++ b/client/X11/xf_client.c
@@ -145,7 +145,8 @@ static const struct xf_exit_code_map_t xf_exit_code_map[] = {
 	{ FREERDP_ERROR_CONNECT_ACCOUNT_RESTRICTION, XF_EXIT_CONNECT_ACCOUNT_RESTRICTION },
 	{ FREERDP_ERROR_CONNECT_ACCOUNT_EXPIRED, XF_EXIT_CONNECT_ACCOUNT_EXPIRED },
 	{ FREERDP_ERROR_CONNECT_LOGON_TYPE_NOT_GRANTED, XF_EXIT_CONNECT_LOGON_TYPE_NOT_GRANTED },
-	{ FREERDP_ERROR_CONNECT_NO_OR_MISSING_CREDENTIALS, XF_EXIT_CONNECT_NO_OR_MISSING_CREDENTIALS }
+	{ FREERDP_ERROR_CONNECT_NO_OR_MISSING_CREDENTIALS, XF_EXIT_CONNECT_NO_OR_MISSING_CREDENTIALS },
+	{ FREERDP_ERROR_CONNECT_TARGET_BOOTING, XF_EXIT_CONNECT_TARGET_BOOTING }
 };
 
 static BOOL xf_setup_x11(xfContext* xfc);
@@ -1708,8 +1709,7 @@ end:
 
 int xf_exit_code_from_disconnect_reason(DWORD reason)
 {
-	if (reason == 0 ||
-	    (reason >= XF_EXIT_PARSE_ARGUMENTS && reason <= XF_EXIT_CONNECT_NO_OR_MISSING_CREDENTIALS))
+	if ((reason == 0) || ((reason >= XF_EXIT_PARSE_ARGUMENTS) && (reason <= XF_EXIT_CODE_LAST)))
 		return WINPR_ASSERTING_INT_CAST(int, reason);
 	/* License error set */
 	else if (reason >= 0x100 && reason <= 0x10A)
diff --git a/client/X11/xfreerdp.h b/client/X11/xfreerdp.h
index 1babfb30b..2ae744f33 100644
--- a/client/X11/xfreerdp.h
+++ b/client/X11/xfreerdp.h
@@ -393,7 +393,8 @@ enum XF_EXIT_CODE
 	XF_EXIT_CONNECT_ACCOUNT_EXPIRED = 157,
 	XF_EXIT_CONNECT_LOGON_TYPE_NOT_GRANTED = 158,
 	XF_EXIT_CONNECT_NO_OR_MISSING_CREDENTIALS = 159,
-
+	XF_EXIT_CONNECT_TARGET_BOOTING = 160,
+	XF_EXIT_CODE_LAST = XF_EXIT_CONNECT_TARGET_BOOTING,
 	XF_EXIT_UNKNOWN = 255,
 };
 
diff --git a/include/freerdp/error.h b/include/freerdp/error.h
index 58f931624..0b64c9ddc 100644
--- a/include/freerdp/error.h
+++ b/include/freerdp/error.h
@@ -270,6 +270,7 @@ extern "C"
 #define ERRCONNECT_LOGON_TYPE_NOT_GRANTED 0x0000001A
 #define ERRCONNECT_NO_OR_MISSING_CREDENTIALS 0x0000001B
 #define ERRCONNECT_ACTIVATION_TIMEOUT 0x0000001C
+#define ERRCONNECT_TARGET_BOOTING 0x0000001D
 
 #define ERRCONNECT_SUCCESS ERRINFO_SUCCESS
 #define ERRCONNECT_NONE ERRINFO_NONE
@@ -352,6 +353,7 @@ extern "C"
 
 #define FREERDP_ERROR_CONNECT_ACTIVATION_TIMEOUT \
 	MAKE_FREERDP_ERROR(CONNECT, ERRCONNECT_ACTIVATION_TIMEOUT)
+#define FREERDP_ERROR_CONNECT_TARGET_BOOTING MAKE_FREERDP_ERROR(CONNECT, ERRCONNECT_TARGET_BOOTING)
 
 #ifdef __cplusplus
 }
diff --git a/libfreerdp/core/errconnect.c b/libfreerdp/core/errconnect.c
index 5fc62748f..333f0fa50 100644
--- a/libfreerdp/core/errconnect.c
+++ b/libfreerdp/core/errconnect.c
@@ -94,6 +94,8 @@
 
 #define ERRCONNECT_ACTIVATION_TIMEOUT_STRING "Timeout waiting for activation."
 
+#define ERRCONNECT_TARGET_BOOTING_STRING "Starting your VM. It may take up to 5 minutes."
+
 /* Special codes */
 #define ERRCONNECT_SUCCESS_STRING "Success."
 #define ERRCONNECT_NONE_STRING ""
@@ -129,6 +131,7 @@ static const ERRINFO ERRCONNECT_CODES[] = {
 	ERRCONNECT_DEFINE(LOGON_TYPE_NOT_GRANTED, CAT_ADMIN),
 	ERRCONNECT_DEFINE(NO_OR_MISSING_CREDENTIALS, CAT_USE),
 	ERRCONNECT_DEFINE(ACTIVATION_TIMEOUT, CAT_PROTOCOL),
+	ERRCONNECT_DEFINE(TARGET_BOOTING, CAT_ADMIN),
 
 	ERRCONNECT_DEFINE(NONE, CAT_NONE)
 };
diff --git a/libfreerdp/core/gateway/arm.c b/libfreerdp/core/gateway/arm.c
index 69f0548dd..3f9ad014d 100644
--- a/libfreerdp/core/gateway/arm.c
+++ b/libfreerdp/core/gateway/arm.c
@@ -1049,6 +1049,7 @@ static BOOL arm_handle_bad_request(rdpArm* arm, const HttpResponse* response, BO
 			WLog_WARN(TAG, "Starting your VM. It may take up to 5 minutes");
 		else
 			WLog_WARN(TAG, "%s", msgstr);
+		freerdp_set_last_error_if_not(arm->context, FREERDP_ERROR_CONNECT_TARGET_BOOTING);
 	}
 	else
 	{
diff --git a/libfreerdp/core/transport.c b/libfreerdp/core/transport.c
index b3ab34e82..9b2a529f3 100644
--- a/libfreerdp/core/transport.c
+++ b/libfreerdp/core/transport.c
@@ -478,6 +478,17 @@ BOOL transport_connect_aad(rdpTransport* transport)
 	return rdp_client_transition_to_state(rdp, CONNECTION_STATE_AAD);
 }
 
+static BOOL transport_can_retry(const rdpContext* context, BOOL status)
+{
+	switch (freerdp_get_last_error(context))
+	{
+		case FREERDP_ERROR_CONNECT_TARGET_BOOTING:
+			return FALSE;
+		default:
+			return status;
+	}
+}
+
 BOOL transport_connect(rdpTransport* transport, const char* hostname, UINT16 port, DWORD timeout)
 {
 	BOOL status = FALSE;
@@ -519,7 +530,7 @@ BOOL transport_connect(rdpTransport* transport, const char* hostname, UINT16 por
 				transport->wst = NULL;
 			}
 		}
-		if (!status && settings->GatewayHttpTransport)
+		if (transport_can_retry(transport->context, status) && settings->GatewayHttpTransport)
 		{
 			WINPR_ASSERT(!transport->rdg);
 			transport->rdg = rdg_new(context);
@@ -544,7 +555,8 @@ BOOL transport_connect(rdpTransport* transport, const char* hostname, UINT16 por
 			}
 		}
 
-		if (!status && settings->GatewayRpcTransport && rpcFallback)
+		if (transport_can_retry(transport->context, status) && settings->GatewayRpcTransport &&
+		    rpcFallback)
 		{
 			WINPR_ASSERT(!transport->tsg);
 			transport->tsg = tsg_new(transport);