diff --git a/client/X11/xf_keyboard.c b/client/X11/xf_keyboard.c
index efd091c2f..6641257e2 100644
--- a/client/X11/xf_keyboard.c
+++ b/client/X11/xf_keyboard.c
@@ -23,7 +23,9 @@
 #include <stdio.h>
 #include <stdlib.h>
 #include <string.h>
+#include <stdint.h>
 
+#include <winpr/assert.h>
 #include <winpr/crt.h>
 #include <winpr/path.h>
 #include <winpr/assert.h>
@@ -191,6 +193,7 @@ void xf_keyboard_release_all_keypress(xfContext* xfc)
 {
 	WINPR_ASSERT(xfc);
 
+	WINPR_STATIC_ASSERT(ARRAYSIZE(xfc->KeyboardState) <= UINT32_MAX);
 	for (size_t keycode = 0; keycode < ARRAYSIZE(xfc->KeyboardState); keycode++)
 	{
 		if (xfc->KeyboardState[keycode])
diff --git a/libfreerdp/locale/keyboard.c b/libfreerdp/locale/keyboard.c
index d8f00e0b1..9de4489eb 100644
--- a/libfreerdp/locale/keyboard.c
+++ b/libfreerdp/locale/keyboard.c
@@ -21,7 +21,9 @@
 
 #include <stdio.h>
 #include <string.h>
+#include <stdint.h>
 
+#include <winpr/assert.h>
 #include <winpr/crt.h>
 
 #include <freerdp/utils/string.h>
@@ -324,6 +326,7 @@ DWORD freerdp_keyboard_init(DWORD keyboardLayoutId)
 
 	ZeroMemory(VIRTUAL_SCANCODE_TO_X11_KEYCODE, sizeof(VIRTUAL_SCANCODE_TO_X11_KEYCODE));
 
+	WINPR_STATIC_ASSERT(ARRAYSIZE(VIRTUAL_SCANCODE_TO_X11_KEYCODE) <= UINT32_MAX);
 	for (size_t keycode = 0; keycode < ARRAYSIZE(VIRTUAL_SCANCODE_TO_X11_KEYCODE); keycode++)
 	{
 		const DWORD x11 = X11_KEYCODE_TO_VIRTUAL_SCANCODE[keycode];
diff --git a/server/shadow/shadow_server.c b/server/shadow/shadow_server.c
index a47d4a568..1045d3a99 100644
--- a/server/shadow/shadow_server.c
+++ b/server/shadow/shadow_server.c
@@ -21,7 +21,9 @@
 #include <freerdp/config.h>
 
 #include <errno.h>
+#include <stdint.h>
 
+#include <winpr/assert.h>
 #include <winpr/crt.h>
 #include <winpr/ssl.h>
 #include <winpr/path.h>
@@ -797,6 +799,8 @@ static BOOL shadow_server_create_certificate(rdpShadowServer* server, const char
 {
 	BOOL rc = FALSE;
 	char* makecert_argv[6] = { "makecert", "-rdp", "-live", "-silent", "-y", "5" };
+
+	WINPR_STATIC_ASSERT(ARRAYSIZE(makecert_argv) <= INT_MAX);
 	const size_t makecert_argc = ARRAYSIZE(makecert_argv);
 
 	MAKECERT_CONTEXT* makecert = makecert_context_new();
@@ -804,7 +808,6 @@ static BOOL shadow_server_create_certificate(rdpShadowServer* server, const char
 	if (!makecert)
 		goto out_fail;
 
-	WINPR_ASSERT(makecert_argc <= INT_MAX);
 	if (makecert_context_process(makecert, (int)makecert_argc, makecert_argv) < 0)
 		goto out_fail;
 
diff --git a/winpr/include/config/wtypes.h.in b/winpr/include/config/wtypes.h.in
index 6d42d890a..67aee9404 100644
--- a/winpr/include/config/wtypes.h.in
+++ b/winpr/include/config/wtypes.h.in
@@ -22,32 +22,6 @@
 
 #include <winpr/platform.h>
 
-// C99 related macros
-#if defined(__STDC__) && defined(__STDC_VERSION__) && (__STDC_VERSION__ >= 199901L)
-#define WINPR_RESTRICT restrict
-#elif defined(_MSC_VER) && _MSC_VER >= 1900
-#define WINPR_RESTRICT __restrict
-#else
-#define WINPR_RESTRICT
-#endif
-
-// C23 related macros
-#if defined(__STDC__) && defined(__STDC_VERSION__) && (__STDC_VERSION__ >= 202311L)
-#define WINPR_FALLTHROUGH \
-	(void)0;              \
-	[[fallthrough]];
-#elif defined(__clang__)
-#define WINPR_FALLTHROUGH \
-	(void)0;              \
-	__attribute__((fallthrough));
-#elif defined(__GNUC__) && (__GNUC__ >= 7)
-#define WINPR_FALLTHROUGH \
-	(void)0;              \
-	__attribute__((fallthrough));
-#else
-#define WINPR_FALLTHROUGH (void)0;
-#endif
-
 /* Set by CMake during configuration */
 #cmakedefine WINPR_HAVE_STDINT_H
 #cmakedefine WINPR_HAVE_STDBOOL_H
diff --git a/winpr/include/winpr/assert.h b/winpr/include/winpr/assert.h
index af8daac73..9d4d2a4b0 100644
--- a/winpr/include/winpr/assert.h
+++ b/winpr/include/winpr/assert.h
@@ -22,6 +22,8 @@
 #define WINPR_ASSERT_H
 
 #include <stdlib.h>
+#include <assert.h>
+
 #include <winpr/winpr.h>
 #include <winpr/wtypes.h>
 #include <winpr/wlog.h>
@@ -56,8 +58,28 @@ extern "C"
 #endif
 
 #else
-#include <assert.h>
 #define WINPR_ASSERT(cond) assert(cond)
 #endif
 
+#ifdef __cplusplus
+extern "C"
+{
+#endif
+#if defined(__cplusplus) && (__cplusplus >= 201703L) // C++ 17
+#define WINPR_STATIC_ASSERT(cond) static_assert(cond)
+#elif defined(__cplusplus) && (__cplusplus >= 201103L) // C++ 11
+#define WINPR_STATIC_ASSERT(cond) static_assert(cond, #cond)
+#elif defined(__STDC_VERSION__) && (__STDC_VERSION__ >= 202311L) // C23
+#define WINPR_STATIC_ASSERT(cond) static_assert(cond)
+#elif defined(__STDC_VERSION__) && (__STDC_VERSION__ >= 201112L) // C11
+#define WINPR_STATIC_ASSERT(cond) _Static_assert(cond, #cond)
+#else
+WINPR_PRAGMA_WARNING("static-assert macro not supported on this platform")
+#define WINPR_STATIC_ASSERT(cond) assert(cond)
+#endif
+
+#ifdef __cplusplus
+}
+#endif
+
 #endif /* WINPR_ERROR_H */
diff --git a/winpr/include/winpr/platform.h b/winpr/include/winpr/platform.h
index 07b10046d..8483996e9 100644
--- a/winpr/include/winpr/platform.h
+++ b/winpr/include/winpr/platform.h
@@ -27,8 +27,36 @@
 #define WINPR_PRAGMA_WARNING(msg) WINPR_DO_PRAGMA(GCC warning #msg)
 #elif defined(__clang__)
 #define WINPR_PRAGMA_WARNING(msg) WINPR_DO_PRAGMA(GCC warning #msg)
-#elif defined(_MSC_VER)
+#elif defined(_MSC_VER) && (_MSC_VER >= 1920)
 #define WINPR_PRAGMA_WARNING(msg) WINPR_DO_PRAGMA(message \x28 #msg \x29)
+#else
+#define WINPR_PRAGMA_WARNING(msg)
+#endif
+
+// C99 related macros
+#if defined(__STDC_VERSION__) && (__STDC_VERSION__ >= 199901L)
+#define WINPR_RESTRICT restrict
+#elif defined(_MSC_VER) && _MSC_VER >= 1900
+#define WINPR_RESTRICT __restrict
+#else
+#define WINPR_RESTRICT
+#endif
+
+// C23 related macros
+#if defined(__STDC_VERSION__) && (__STDC_VERSION__ >= 202311L)
+#define WINPR_FALLTHROUGH \
+	(void)0;              \
+	[[fallthrough]];
+#elif defined(__clang__)
+#define WINPR_FALLTHROUGH \
+	(void)0;              \
+	__attribute__((fallthrough));
+#elif defined(__GNUC__) && (__GNUC__ >= 7)
+#define WINPR_FALLTHROUGH \
+	(void)0;              \
+	__attribute__((fallthrough));
+#else
+#define WINPR_FALLTHROUGH (void)0;
 #endif
 
 #if defined(__clang__)
diff --git a/winpr/include/winpr/winpr.h b/winpr/include/winpr/winpr.h
index 715231f9a..16af05c51 100644
--- a/winpr/include/winpr/winpr.h
+++ b/winpr/include/winpr/winpr.h
@@ -65,7 +65,7 @@
 #define WINPR_FORMAT_ARG _Printf_format_string_
 #endif
 
-#if defined(__STDC__) && defined(__STDC_VERSION__) && (__STDC_VERSION__ >= 202311L)
+#if defined(__STDC_VERSION__) && (__STDC_VERSION__ >= 202311L)
 #define WINPR_DEPRECATED(obj) [[deprecated]] obj
 #define WINPR_DEPRECATED_VAR(text, obj) [[deprecated(text)]] obj
 #define WINPR_NORETURN(obj) [[noreturn]] obj