diff --git a/libfreerdp/common/assistance.c b/libfreerdp/common/assistance.c
index 97770b8f1..212e8467b 100644
--- a/libfreerdp/common/assistance.c
+++ b/libfreerdp/common/assistance.c
@@ -1397,7 +1397,9 @@ static BOOL setup_string(wArrayList* list)
 
 rdpAssistanceFile* freerdp_assistance_file_new(void)
 {
-	winpr_InitializeSSL(WINPR_SSL_INIT_DEFAULT);
+	if (!winpr_InitializeSSL(WINPR_SSL_INIT_DEFAULT))
+		return nullptr;
+
 	rdpAssistanceFile* file = calloc(1, sizeof(rdpAssistanceFile));
 	if (!file)
 		return nullptr;
diff --git a/libfreerdp/common/test/TestCommonAssistance.c b/libfreerdp/common/test/TestCommonAssistance.c
index 4a6ce2557..f62faa9f6 100644
--- a/libfreerdp/common/test/TestCommonAssistance.c
+++ b/libfreerdp/common/test/TestCommonAssistance.c
@@ -286,11 +286,11 @@ static BOOL test_msrsc_incident_file_type2(wLog* log)
 
 int TestCommonAssistance(int argc, char* argv[])
 {
-	wLog* log = nullptr;
 	WINPR_UNUSED(argc);
 	WINPR_UNUSED(argv);
-	log = WLog_Get(__func__);
-	winpr_InitializeSSL(WINPR_SSL_INIT_DEFAULT);
+	wLog* log = WLog_Get(__func__);
+	if (!winpr_InitializeSSL(WINPR_SSL_INIT_DEFAULT))
+		return -1;
 
 	for (size_t x = 0; x < ARRAYSIZE(fail_tests); x++)
 	{
diff --git a/server/Sample/sfreerdp.c b/server/Sample/sfreerdp.c
index daafec5c6..569f7640a 100644
--- a/server/Sample/sfreerdp.c
+++ b/server/Sample/sfreerdp.c
@@ -1479,7 +1479,9 @@ int main(int argc, char* argv[])
 	}
 
 	WTSRegisterWtsApiFunctionTable(FreeRDP_InitWtsApi());
-	winpr_InitializeSSL(WINPR_SSL_INIT_DEFAULT);
+	if (!winpr_InitializeSSL(WINPR_SSL_INIT_DEFAULT))
+		return -1;
+
 	instance = freerdp_listener_new();
 
 	if (!instance)
diff --git a/server/proxy/pf_server.c b/server/proxy/pf_server.c
index 4d645d1ec..db0e2e5df 100644
--- a/server/proxy/pf_server.c
+++ b/server/proxy/pf_server.c
@@ -813,7 +813,8 @@ BOOL pf_server_start(proxyServer* server)
 	WINPR_ASSERT(server);
 
 	WTSRegisterWtsApiFunctionTable(FreeRDP_InitWtsApi());
-	winpr_InitializeSSL(WINPR_SSL_INIT_DEFAULT);
+	if (!winpr_InitializeSSL(WINPR_SSL_INIT_DEFAULT))
+		goto error;
 
 	if (WSAStartup(MAKEWORD(2, 2), &wsaData) != 0)
 		goto error;
@@ -853,7 +854,8 @@ BOOL pf_server_start_from_socket(proxyServer* server, int socket)
 	WINPR_ASSERT(server);
 
 	WTSRegisterWtsApiFunctionTable(FreeRDP_InitWtsApi());
-	winpr_InitializeSSL(WINPR_SSL_INIT_DEFAULT);
+	if (!winpr_InitializeSSL(WINPR_SSL_INIT_DEFAULT))
+		goto error;
 
 	if (WSAStartup(MAKEWORD(2, 2), &wsaData) != 0)
 		goto error;
diff --git a/winpr/libwinpr/crypto/test/TestCryptoCipher.c b/winpr/libwinpr/crypto/test/TestCryptoCipher.c
index 200df7885..bd6548f06 100644
--- a/winpr/libwinpr/crypto/test/TestCryptoCipher.c
+++ b/winpr/libwinpr/crypto/test/TestCryptoCipher.c
@@ -233,7 +233,8 @@ int TestCryptoCipher(int argc, char* argv[])
 	WINPR_UNUSED(argc);
 	WINPR_UNUSED(argv);
 
-	winpr_InitializeSSL(WINPR_SSL_INIT_DEFAULT);
+	if (!winpr_InitializeSSL(WINPR_SSL_INIT_DEFAULT))
+		return -1;
 
 	if (!test_crypto_cipher_aes_128_cbc(TRUE))
 		return -1;
diff --git a/winpr/libwinpr/crypto/test/TestCryptoHash.c b/winpr/libwinpr/crypto/test/TestCryptoHash.c
index a1aea53fa..b6a4c653f 100644
--- a/winpr/libwinpr/crypto/test/TestCryptoHash.c
+++ b/winpr/libwinpr/crypto/test/TestCryptoHash.c
@@ -297,7 +297,8 @@ int TestCryptoHash(int argc, char* argv[])
 	WINPR_UNUSED(argc);
 	WINPR_UNUSED(argv);
 
-	winpr_InitializeSSL(WINPR_SSL_INIT_DEFAULT);
+	if (!winpr_InitializeSSL(WINPR_SSL_INIT_DEFAULT))
+		return -1;
 
 	if (!test_crypto_hash_md5())
 		return -1;
diff --git a/winpr/libwinpr/crypto/test/TestCryptoProtectMemory.c b/winpr/libwinpr/crypto/test/TestCryptoProtectMemory.c
index 828dfb346..1a8da0734 100644
--- a/winpr/libwinpr/crypto/test/TestCryptoProtectMemory.c
+++ b/winpr/libwinpr/crypto/test/TestCryptoProtectMemory.c
@@ -9,6 +9,7 @@ static const char* SECRET_PASSWORD_TEST = "MySecretPassword123!";
 
 int TestCryptoProtectMemory(int argc, char* argv[])
 {
+	int rc = -1;
 	UINT32 cbPlainText = 0;
 	UINT32 cbCipherText = 0;
 	const char* pPlainText = nullptr;
@@ -30,12 +31,13 @@ int TestCryptoProtectMemory(int argc, char* argv[])
 	}
 	CopyMemory(pCipherText, pPlainText, cbPlainText);
 	ZeroMemory(&pCipherText[cbPlainText], (cbCipherText - cbPlainText));
-	winpr_InitializeSSL(WINPR_SSL_INIT_DEFAULT);
+	if (!winpr_InitializeSSL(WINPR_SSL_INIT_DEFAULT))
+		goto fail;
 
 	if (!CryptProtectMemory(pCipherText, cbCipherText, CRYPTPROTECTMEMORY_SAME_PROCESS))
 	{
 		printf("CryptProtectMemory failure\n");
-		return -1;
+		goto fail;
 	}
 
 	printf("PlainText: %s (cbPlainText = %" PRIu32 ", cbCipherText = %" PRIu32 ")\n", pPlainText,
@@ -45,11 +47,14 @@ int TestCryptoProtectMemory(int argc, char* argv[])
 	if (!CryptUnprotectMemory(pCipherText, cbCipherText, CRYPTPROTECTMEMORY_SAME_PROCESS))
 	{
 		printf("CryptUnprotectMemory failure\n");
-		return -1;
+		goto fail;
 	}
 
 	printf("Decrypted CipherText: %s\n", pCipherText);
 	SecureZeroMemory(pCipherText, cbCipherText);
+
+	rc = 0;
+fail:
 	free(pCipherText);
-	return 0;
+	return rc;
 }
diff --git a/winpr/libwinpr/sspi/Schannel/schannel_openssl.c b/winpr/libwinpr/sspi/Schannel/schannel_openssl.c
index 231238ff1..bcec783cf 100644
--- a/winpr/libwinpr/sspi/Schannel/schannel_openssl.c
+++ b/winpr/libwinpr/sspi/Schannel/schannel_openssl.c
@@ -587,12 +587,13 @@ SECURITY_STATUS schannel_openssl_decrypt_message(SCHANNEL_OPENSSL* context, PSec
 
 SCHANNEL_OPENSSL* schannel_openssl_new(void)
 {
-	SCHANNEL_OPENSSL* context = nullptr;
-	context = (SCHANNEL_OPENSSL*)calloc(1, sizeof(SCHANNEL_OPENSSL));
+	if (!winpr_InitializeSSL(WINPR_SSL_INIT_DEFAULT))
+		return nullptr;
+
+	SCHANNEL_OPENSSL* context = (SCHANNEL_OPENSSL*)calloc(1, sizeof(SCHANNEL_OPENSSL));
 
 	if (context != nullptr)
 	{
-		winpr_InitializeSSL(WINPR_SSL_INIT_DEFAULT);
 		context->connected = FALSE;
 	}
 
diff --git a/winpr/libwinpr/sspi/sspi_winpr.c b/winpr/libwinpr/sspi/sspi_winpr.c
index bfe2c606c..3a308b0ef 100644
--- a/winpr/libwinpr/sspi/sspi_winpr.c
+++ b/winpr/libwinpr/sspi/sspi_winpr.c
@@ -972,7 +972,8 @@ static BOOL WINPR_init(void)
 static BOOL CALLBACK sspi_init(WINPR_ATTR_UNUSED PINIT_ONCE InitOnce,
                                WINPR_ATTR_UNUSED PVOID Parameter, WINPR_ATTR_UNUSED PVOID* Context)
 {
-	winpr_InitializeSSL(WINPR_SSL_INIT_DEFAULT);
+	if (!winpr_InitializeSSL(WINPR_SSL_INIT_DEFAULT))
+		return FALSE;
 	sspi_ContextBufferAllocTableNew();
 	if (!SCHANNEL_init())
 		return FALSE;
diff --git a/winpr/tools/hash-cli/hash.c b/winpr/tools/hash-cli/hash.c
index c6223726b..78d9e132b 100644
--- a/winpr/tools/hash-cli/hash.c
+++ b/winpr/tools/hash-cli/hash.c
@@ -153,7 +153,11 @@ int main(int argc, char* argv[])
 		printf("missing username or password\n\n");
 		return usage_and_exit();
 	}
-	winpr_InitializeSSL(WINPR_SSL_INIT_DEFAULT);
+	if (!winpr_InitializeSSL(WINPR_SSL_INIT_DEFAULT))
+	{
+		printf("winpr_InitializeSSL failed\n\n");
+		return usage_and_exit();
+	}
 
 	UserLength = strlen(User);
 	PasswordLength = strlen(Password);