diff --git a/server/shadow/CMakeLists.txt b/server/shadow/CMakeLists.txt
index 51b5f9089..c5a104768 100644
--- a/server/shadow/CMakeLists.txt
+++ b/server/shadow/CMakeLists.txt
@@ -115,6 +115,8 @@ if(WITH_X11)
 	endif()
 endif()
 
+include_directories(${OPENSSL_INCLUDE_DIR})
+
 set(${MODULE_PREFIX}_SRCS
 	shadow_client.c
 	shadow_client.h
diff --git a/server/shadow/shadow_client.c b/server/shadow/shadow_client.c
index 17cb13533..a66049944 100644
--- a/server/shadow/shadow_client.c
+++ b/server/shadow/shadow_client.c
@@ -53,6 +53,8 @@ void shadow_client_context_new(freerdp_peer* peer, rdpShadowClient* client)
 	settings->CertificateFile = _strdup(server->CertificateFile);
 	settings->PrivateKeyFile = _strdup(server->PrivateKeyFile);
 
+	settings->RdpKeyFile = _strdup(settings->PrivateKeyFile);
+
 	client->inLobby = TRUE;
 	client->mayView = server->mayView;
 	client->mayInteract = server->mayInteract;
diff --git a/server/shadow/shadow_server.c b/server/shadow/shadow_server.c
index 9d2ecb6ec..22949822b 100644
--- a/server/shadow/shadow_server.c
+++ b/server/shadow/shadow_server.c
@@ -21,6 +21,7 @@
 #endif
 
 #include <winpr/crt.h>
+#include <winpr/ssl.h>
 #include <winpr/wnd.h>
 #include <winpr/path.h>
 #include <winpr/cmdline.h>
@@ -30,6 +31,10 @@
 
 #include <winpr/tools/makecert.h>
 
+#ifdef _WIN32
+#include <openssl/applink.c>
+#endif
+
 #ifndef _WIN32
 #include <sys/select.h>
 #include <sys/signal.h>
@@ -420,6 +425,8 @@ int shadow_server_init(rdpShadowServer* server)
 {
 	int status;
 
+	winpr_InitializeSSL(WINPR_SSL_INIT_DEFAULT);
+
 	WTSRegisterWtsApiFunctionTable(FreeRDP_InitWtsApi());
 
 	server->StopEvent = CreateEvent(NULL, TRUE, FALSE, NULL);