diff --git a/client/Wayland/wlf_input.c b/client/Wayland/wlf_input.c
index 20f3c21f3..a3f5a6a25 100644
--- a/client/Wayland/wlf_input.c
+++ b/client/Wayland/wlf_input.c
@@ -340,7 +340,7 @@ BOOL wlf_handle_key(freerdp* instance, const UwacKeyEvent* ev)
 	if (rdp_scancode == RDP_SCANCODE_UNKNOWN)
 		return TRUE;
 
-	return freerdp_input_send_keyboard_event_ex(input, ev->pressed, rdp_scancode);
+	return freerdp_input_send_keyboard_event_ex(input, ev->pressed, ev->repeated, rdp_scancode);
 }
 
 BOOL wlf_handle_ungrab_key(freerdp* instance, const UwacKeyEvent* ev)
diff --git a/client/Windows/wf_event.c b/client/Windows/wf_event.c
index 1debb4704..2433a5bd6 100644
--- a/client/Windows/wf_event.c
+++ b/client/Windows/wf_event.c
@@ -64,8 +64,11 @@ LRESULT CALLBACK wf_ll_kbd_proc(int nCode, WPARAM wParam, LPARAM lParam)
 
 	wfContext* wfc = NULL;
 	DWORD rdp_scancode;
+	BOOL keystate;
 	rdpInput* input;
 	PKBDLLHOOKSTRUCT p;
+
+	static BOOL keystates[256] = { 0 };
 	DEBUG_KBD("Low-level keyboard hook, hWnd %X nCode %X wParam %X", g_focus_hWnd, nCode, wParam);
 
 	if (g_flipping_in)
@@ -110,6 +113,20 @@ LRESULT CALLBACK wf_ll_kbd_proc(int nCode, WPARAM wParam, LPARAM lParam)
 
 				input = wfc->common.context.input;
 				rdp_scancode = MAKE_RDP_SCANCODE((BYTE)p->scanCode, p->flags & LLKHF_EXTENDED);
+				keystate = keystates[p->scanCode & 0xFF];
+
+				switch (wParam)
+				{
+					case WM_KEYDOWN:
+					case WM_SYSKEYDOWN:
+						keystates[p->scanCode & 0xFF] = TRUE;
+						break;
+					case WM_KEYUP:
+					case WM_SYSKEYUP:
+					default:
+						keystates[p->scanCode & 0xFF] = FALSE;
+						break;
+				}
 				DEBUG_KBD("keydown %d scanCode 0x%08lX flags 0x%08lX vkCode 0x%08lX",
 				          (wParam == WM_KEYDOWN), p->scanCode, p->flags, p->vkCode);
 
@@ -138,10 +155,14 @@ LRESULT CALLBACK wf_ll_kbd_proc(int nCode, WPARAM wParam, LPARAM lParam)
 					if (wParam == WM_KEYDOWN)
 					{
 						DEBUG_KBD("Pause, sent as Ctrl+NumLock");
-						freerdp_input_send_keyboard_event_ex(input, TRUE, RDP_SCANCODE_LCONTROL);
-						freerdp_input_send_keyboard_event_ex(input, TRUE, RDP_SCANCODE_NUMLOCK);
-						freerdp_input_send_keyboard_event_ex(input, FALSE, RDP_SCANCODE_LCONTROL);
-						freerdp_input_send_keyboard_event_ex(input, FALSE, RDP_SCANCODE_NUMLOCK);
+						freerdp_input_send_keyboard_event_ex(input, TRUE, FALSE,
+						                                     RDP_SCANCODE_LCONTROL);
+						freerdp_input_send_keyboard_event_ex(input, TRUE, FALSE,
+						                                     RDP_SCANCODE_NUMLOCK);
+						freerdp_input_send_keyboard_event_ex(input, FALSE, FALSE,
+						                                     RDP_SCANCODE_LCONTROL);
+						freerdp_input_send_keyboard_event_ex(input, FALSE, FALSE,
+						                                     RDP_SCANCODE_NUMLOCK);
 					}
 					else
 					{
@@ -156,7 +177,8 @@ LRESULT CALLBACK wf_ll_kbd_proc(int nCode, WPARAM wParam, LPARAM lParam)
 					rdp_scancode = RDP_SCANCODE_RSHIFT;
 				}
 
-				freerdp_input_send_keyboard_event_ex(input, !(p->flags & LLKHF_UP), rdp_scancode);
+				freerdp_input_send_keyboard_event_ex(input, !(p->flags & LLKHF_UP), keystate,
+				                                     rdp_scancode);
 
 				if (p->vkCode == VK_NUMLOCK || p->vkCode == VK_CAPITAL || p->vkCode == VK_SCROLL ||
 				    p->vkCode == VK_KANA)
@@ -165,6 +187,8 @@ LRESULT CALLBACK wf_ll_kbd_proc(int nCode, WPARAM wParam, LPARAM lParam)
 				else
 					return 1;
 
+				break;
+			default:
 				break;
 		}
 	}
diff --git a/client/X11/xf_keyboard.c b/client/X11/xf_keyboard.c
index 924473b5c..e1c520771 100644
--- a/client/X11/xf_keyboard.c
+++ b/client/X11/xf_keyboard.c
@@ -62,7 +62,7 @@ BOOL xf_keyboard_update_modifier_map(xfContext* xfc)
 	return xfc->modifierMap != NULL;
 }
 
-static void xf_keyboard_send_key(xfContext* xfc, BOOL down, const XKeyEvent* ev);
+static void xf_keyboard_send_key(xfContext* xfc, BOOL down, BOOL repeat, const XKeyEvent* ev);
 
 static BOOL xf_sync_kbd_state(xfContext* xfc)
 {
@@ -175,18 +175,21 @@ void xf_keyboard_free(xfContext* xfc)
 
 void xf_keyboard_key_press(xfContext* xfc, const XKeyEvent* event, KeySym keysym)
 {
+	BOOL last;
+
 	WINPR_ASSERT(xfc);
 	WINPR_ASSERT(event);
 
 	if (event->keycode < 8)
 		return;
 
+	last = xfc->KeyboardState[event->keycode];
 	xfc->KeyboardState[event->keycode] = TRUE;
 
 	if (xf_keyboard_handle_special_keys(xfc, keysym))
 		return;
 
-	xf_keyboard_send_key(xfc, TRUE, event);
+	xf_keyboard_send_key(xfc, TRUE, last, event);
 }
 
 void xf_keyboard_key_release(xfContext* xfc, const XKeyEvent* event, KeySym keysym)
@@ -197,9 +200,10 @@ void xf_keyboard_key_release(xfContext* xfc, const XKeyEvent* event, KeySym keys
 	if (event->keycode < 8)
 		return;
 
+	BOOL last = xfc->KeyboardState[event->keycode];
 	xfc->KeyboardState[event->keycode] = FALSE;
 	xf_keyboard_handle_special_keys_release(xfc, keysym);
-	xf_keyboard_send_key(xfc, FALSE, event);
+	xf_keyboard_send_key(xfc, FALSE, last, event);
 }
 
 void xf_keyboard_release_all_keypress(xfContext* xfc)
@@ -218,10 +222,11 @@ void xf_keyboard_release_all_keypress(xfContext* xfc)
 			// release tab before releasing the windows key.
 			// this stops the start menu from opening on unfocus event.
 			if (rdp_scancode == RDP_SCANCODE_LWIN)
-				freerdp_input_send_keyboard_event_ex(xfc->common.context.input, FALSE,
+				freerdp_input_send_keyboard_event_ex(xfc->common.context.input, FALSE, FALSE,
 				                                     RDP_SCANCODE_TAB);
 
-			freerdp_input_send_keyboard_event_ex(xfc->common.context.input, FALSE, rdp_scancode);
+			freerdp_input_send_keyboard_event_ex(xfc->common.context.input, FALSE, FALSE,
+			                                     rdp_scancode);
 			xfc->KeyboardState[keycode] = FALSE;
 		}
 	}
@@ -234,7 +239,7 @@ BOOL xf_keyboard_key_pressed(xfContext* xfc, KeySym keysym)
 	return xfc->KeyboardState[keycode];
 }
 
-void xf_keyboard_send_key(xfContext* xfc, BOOL down, const XKeyEvent* event)
+void xf_keyboard_send_key(xfContext* xfc, BOOL down, BOOL repeat, const XKeyEvent* event)
 {
 	DWORD rdp_scancode;
 	rdpInput* input;
@@ -290,7 +295,7 @@ void xf_keyboard_send_key(xfContext* xfc, BOOL down, const XKeyEvent* event)
 				if (rdp_scancode == RDP_SCANCODE_UNKNOWN)
 					WLog_ERR(TAG, "Unknown key with X keycode 0x%02" PRIx8 "", event->keycode);
 				else
-					freerdp_input_send_keyboard_event_ex(input, down, rdp_scancode);
+					freerdp_input_send_keyboard_event_ex(input, down, repeat, rdp_scancode);
 			}
 			else
 				freerdp_input_send_unicode_keyboard_event(input, down ? KBD_FLAGS_RELEASE : 0,
@@ -299,7 +304,7 @@ void xf_keyboard_send_key(xfContext* xfc, BOOL down, const XKeyEvent* event)
 		else if (rdp_scancode == RDP_SCANCODE_UNKNOWN)
 			WLog_ERR(TAG, "Unknown key with X keycode 0x%02" PRIx8 "", event->keycode);
 		else
-			freerdp_input_send_keyboard_event_ex(input, down, rdp_scancode);
+			freerdp_input_send_keyboard_event_ex(input, down, repeat, rdp_scancode);
 
 		if ((rdp_scancode == RDP_SCANCODE_CAPSLOCK) && (down == FALSE))
 		{