diff --git a/lib/include/chiaki/common.h b/lib/include/chiaki/common.h
index 03d646d..f0cd66d 100644
--- a/lib/include/chiaki/common.h
+++ b/lib/include/chiaki/common.h
@@ -24,6 +24,8 @@
 #define CHIAKI_SOCKET_IS_INVALID(s) ((s) == INVALID_SOCKET)
 #define CHIAKI_INVALID_SOCKET INVALID_SOCKET
 #define CHIAKI_SOCKET_CLOSE(s) closesocket(s)
+#define CHIAKI_SOCKET_ERROR_FMT "%d"
+#define CHIAKI_SOCKET_ERROR_VALUE (WSAGetLastError())
 #ifndef WIN32_LEAN_AND_MEAN
 #define WIN32_LEAN_AND_MEAN
 #endif
@@ -33,6 +35,8 @@
 #define CHIAKI_SOCKET_IS_INVALID(s) ((s) < 0)
 #define CHIAKI_INVALID_SOCKET (-1)
 #define CHIAKI_SOCKET_CLOSE(s) close(s)
+#define CHIAKI_SOCKET_ERROR_FMT "%s"
+#define CHIAKI_SOCKET_ERROR_VALUE (strerror(errno))
 #endif
 
 #ifdef __cplusplus
diff --git a/lib/include/chiaki/session.h b/lib/include/chiaki/session.h
index 0cd52c0..d090529 100644
--- a/lib/include/chiaki/session.h
+++ b/lib/include/chiaki/session.h
@@ -91,6 +91,7 @@ typedef enum {
 	CHIAKI_QUIT_REASON_SESSION_REQUEST_RP_IN_USE,
 	CHIAKI_QUIT_REASON_SESSION_REQUEST_RP_CRASH,
 	CHIAKI_QUIT_REASON_CTRL_UNKNOWN,
+	CHIAKI_QUIT_REASON_CTRL_CONNECT_FAILED,
 	CHIAKI_QUIT_REASON_CTRL_CONNECTION_REFUSED,
 	CHIAKI_QUIT_REASON_STREAM_CONNECTION_UNKNOWN,
 	CHIAKI_QUIT_REASON_STREAM_CONNECTION_REMOTE_DISCONNECTED
diff --git a/lib/src/ctrl.c b/lib/src/ctrl.c
index c9f7b0e..3409866 100644
--- a/lib/src/ctrl.c
+++ b/lib/src/ctrl.c
@@ -154,7 +154,7 @@ static void *ctrl_thread_func(void *user)
 	ChiakiErrorCode err = ctrl_connect(ctrl);
 	if(err != CHIAKI_ERR_SUCCESS)
 	{
-		ctrl_failed(ctrl, CHIAKI_QUIT_REASON_CTRL_UNKNOWN);
+		ctrl_failed(ctrl, CHIAKI_QUIT_REASON_CTRL_CONNECT_FAILED);
 		return NULL;
 	}
 
@@ -233,7 +233,10 @@ static void *ctrl_thread_func(void *user)
 		if(received <= 0)
 		{
 			if(received < 0)
+			{
+				CHIAKI_LOGE(ctrl->session->log, "Ctrl failed to recv: " CHIAKI_SOCKET_ERROR_FMT, CHIAKI_SOCKET_ERROR_VALUE);
 				ctrl_failed(ctrl, CHIAKI_QUIT_REASON_CTRL_UNKNOWN);
+			}
 			break;
 		}
 
@@ -304,6 +307,10 @@ static void ctrl_message_received(ChiakiCtrl *ctrl, uint16_t msg_type, uint8_t *
 		}
 	}
 
+	CHIAKI_LOGV(ctrl->session->log, "Ctrl received message of type %#x, size %#llx", (unsigned int)msg_type, (unsigned long long)payload_size);
+	if(payload_size > 0)
+		chiaki_log_hexdump(ctrl->session->log, CHIAKI_LOG_VERBOSE, payload, payload_size);
+
 	switch(msg_type)
 	{
 		case CTRL_MESSAGE_TYPE_SESSION_ID:
@@ -409,7 +416,7 @@ static void ctrl_message_received_login(ChiakiCtrl *ctrl, uint8_t *payload, size
 {
 	if(payload_size != 1)
 	{
-		CHIAKI_LOGW(ctrl->session->log, "Ctrl received Login message with payload of size %llx", (unsigned long long)payload_size);
+		CHIAKI_LOGW(ctrl->session->log, "Ctrl received Login message with payload of size %#llx", (unsigned long long)payload_size);
 		if(payload_size < 1)
 			return;
 	}
@@ -436,7 +443,7 @@ static void ctrl_message_received_login(ChiakiCtrl *ctrl, uint8_t *payload, size
 				CHIAKI_LOGW(ctrl->session->log, "Ctrl Login PIN incorrect message, but PIN was not requested");
 			break;
 		default:
-			CHIAKI_LOGI(ctrl->session->log, "Ctrl received Login message with state: %x", state);
+			CHIAKI_LOGI(ctrl->session->log, "Ctrl received Login message with state: %#x", state);
 			break;
 	}
 }
@@ -480,7 +487,10 @@ static ChiakiErrorCode ctrl_connect(ChiakiCtrl *ctrl)
 	struct addrinfo *addr = session->connect_info.host_addrinfo_selected;
 	struct sockaddr *sa = malloc(addr->ai_addrlen);
 	if(!sa)
+	{
+		CHIAKI_LOGE(session->log, "Ctrl failed to alloc sockaddr");
 		return CHIAKI_ERR_MEMORY;
+	}
 	memcpy(sa, addr->ai_addr, addr->ai_addrlen);
 
 	if(sa->sa_family == AF_INET)
@@ -488,10 +498,13 @@ static ChiakiErrorCode ctrl_connect(ChiakiCtrl *ctrl)
 	else if(sa->sa_family == AF_INET6)
 		((struct sockaddr_in6 *)sa)->sin6_port = htons(SESSION_CTRL_PORT);
 	else
+	{
+		CHIAKI_LOGE(session->log, "Ctrl got invalid sockaddr");
 		return CHIAKI_ERR_INVALID_DATA;
+	}
 
 	chiaki_socket_t sock = socket(sa->sa_family, SOCK_STREAM, IPPROTO_TCP);
-	if(sock < 0)
+	if(CHIAKI_SOCKET_IS_INVALID(sock))
 	{
 		CHIAKI_LOGE(session->log, "Session ctrl socket creation failed.");
 		ctrl_failed(ctrl, CHIAKI_QUIT_REASON_CTRL_UNKNOWN);
@@ -502,9 +515,16 @@ static ChiakiErrorCode ctrl_connect(ChiakiCtrl *ctrl)
 	free(sa);
 	if(r < 0)
 	{
+#ifdef _WIN32
+		int errsv = WSAGetLastError();
+		CHIAKI_LOGE(session->log, "Ctrl connect failed: %d", errsv);
+		ChiakiQuitReason quit_reason = errsv == WSAECONNREFUSED ? CHIAKI_QUIT_REASON_CTRL_CONNECTION_REFUSED : CHIAKI_QUIT_REASON_CTRL_UNKNOWN;
+#else
 		int errsv = errno;
 		CHIAKI_LOGE(session->log, "Ctrl connect failed: %s", strerror(errsv));
-		ctrl_failed(ctrl, errsv == ECONNREFUSED ? CHIAKI_QUIT_REASON_CTRL_CONNECTION_REFUSED : CHIAKI_QUIT_REASON_CTRL_UNKNOWN);
+		ChiakiQuitReason quit_reason = errsv == ECONNREFUSED ? CHIAKI_QUIT_REASON_CTRL_CONNECTION_REFUSED : CHIAKI_QUIT_REASON_CTRL_UNKNOWN;
+#endif
+		ctrl_failed(ctrl, quit_reason);
 		CHIAKI_SOCKET_CLOSE(sock);
 		return CHIAKI_ERR_NETWORK;
 	}
@@ -578,10 +598,34 @@ static ChiakiErrorCode ctrl_connect(ChiakiCtrl *ctrl)
 	if(err != CHIAKI_ERR_SUCCESS)
 	{
 		if(err != CHIAKI_ERR_CANCELED)
+		{
+#ifdef _WIN32
+			int errsv = WSAGetLastError;
+#else
+			int errsv = errno;
+#endif
 			CHIAKI_LOGE(session->log, "Failed to receive ctrl request response: %s", chiaki_error_string(err));
+			if(err == CHIAKI_ERR_NETWORK)
+			{
+				CHIAKI_LOGE(session->log, "Ctrl request response network error: " CHIAKI_SOCKET_ERROR_FMT,
+#ifdef _WIN32
+																										errsv
+#else
+																										strerror(errsv)
+#endif
+																										);
+			}
+		}
+		else
+		{
+			CHIAKI_LOGI(session->log, "Ctrl canceled while receiving ctrl request response");
+		}
 		goto error;
 	}
 
+	CHIAKI_LOGI(session->log, "Ctrl received http header as response");
+	chiaki_log_hexdump(session->log, CHIAKI_LOG_VERBOSE, (const uint8_t *)buf, header_size);
+
 	ChiakiHttpResponse http_response;
 	err = chiaki_http_response_parse(&http_response, buf, header_size);
 	if(err != CHIAKI_ERR_SUCCESS)
@@ -590,15 +634,18 @@ static ChiakiErrorCode ctrl_connect(ChiakiCtrl *ctrl)
 		goto error;
 	}
 
+	CHIAKI_LOGI(session->log, "Ctrl received ctrl request http response");
+
 	CtrlResponse response;
 	parse_ctrl_response(&response, &http_response);
-	chiaki_http_response_fini(&http_response);
-
 	if(!response.success)
 	{
+		CHIAKI_LOGE(session->log, "Ctrl http response was not successful. HTTP code was %d", http_response.code);
+		chiaki_http_response_fini(&http_response);
 		err = CHIAKI_ERR_UNKNOWN;
 		goto error;
 	}
+	chiaki_http_response_fini(&http_response);
 
 	if(response.server_type_valid)
 	{
@@ -607,7 +654,11 @@ static ChiakiErrorCode ctrl_connect(ChiakiCtrl *ctrl)
 				response.rp_server_type,
 				response.rp_server_type,
 				sizeof(response.rp_server_type));
-		response.server_type_valid = err2 == CHIAKI_ERR_SUCCESS;
+		if(err2 != CHIAKI_ERR_SUCCESS)
+		{
+			CHIAKI_LOGE(session->log, "Ctrl failed to decrypt RP-Server-Type");
+			response.server_type_valid = false;
+		}
 	}
 
 	if(!response.server_type_valid)
diff --git a/lib/src/http.c b/lib/src/http.c
index 486c908..7e9d000 100644
--- a/lib/src/http.c
+++ b/lib/src/http.c
@@ -164,7 +164,7 @@ CHIAKI_EXPORT ChiakiErrorCode chiaki_recv_http_header(int sock, char *buf, size_
 
 		int received = (int)recv(sock, buf, (int)buf_size, 0);
 		if(received <= 0)
-			return CHIAKI_ERR_NETWORK;
+			return received == 0 ? CHIAKI_ERR_DISCONNECTED : CHIAKI_ERR_NETWORK;
 
 		*received_size += received;
 		for(; received > 0; buf++, received--)
diff --git a/lib/src/session.c b/lib/src/session.c
index af7a1d9..a061ad6 100644
--- a/lib/src/session.c
+++ b/lib/src/session.c
@@ -126,6 +126,8 @@ CHIAKI_EXPORT const char *chiaki_quit_reason_string(ChiakiQuitReason reason)
 			return "Unknown Ctrl Error";
 		case CHIAKI_QUIT_REASON_CTRL_CONNECTION_REFUSED:
 			return "Connection Refused in Ctrl";
+		case CHIAKI_QUIT_REASON_CTRL_CONNECT_FAILED:
+			return "Ctrl failed to connect";
 		case CHIAKI_QUIT_REASON_STREAM_CONNECTION_UNKNOWN:
 			return "Unknown Error in Stream Connection";
 		case CHIAKI_QUIT_REASON_STREAM_CONNECTION_REMOTE_DISCONNECTED:
@@ -363,7 +365,10 @@ static void *session_thread_func(void *arg)
 	CHECK_STOP(quit_ctrl);
 
 	if(session->ctrl_failed)
+	{
+		CHIAKI_LOGE(session->log, "Ctrl has failed while waiting for ctrl startup");
 		goto ctrl_failed;
+	}
 
 	bool pin_incorrect = false;
 	while(session->ctrl_login_pin_requested)
@@ -382,7 +387,10 @@ static void *session_thread_func(void *arg)
 		chiaki_cond_timedwait_pred(&session->state_cond, &session->state_mutex, UINT64_MAX, session_check_state_pred_pin, session);
 		CHECK_STOP(quit_ctrl);
 		if(session->ctrl_failed)
+		{
+			CHIAKI_LOGE(session->log, "Ctrl has failed while waiting for PIN entry");
 			goto ctrl_failed;
+		}
 
 		assert(session->login_pin_entered && session->login_pin);
 		CHIAKI_LOGI(session->log, "Session received entered Login PIN, forwarding to Ctrl");
@@ -399,6 +407,7 @@ static void *session_thread_func(void *arg)
 
 	if(!session->ctrl_session_id_received)
 	{
+		CHIAKI_LOGE(session->log, "Ctrl did not receive session id");
 ctrl_failed:
 		CHIAKI_LOGE(session->log, "Ctrl has failed, shutting down");
 		if(session->quit_reason == CHIAKI_QUIT_REASON_NONE)