diff --git a/Core/FileLoaders/HTTPFileLoader.cpp b/Core/FileLoaders/HTTPFileLoader.cpp
index 4dda285844..f3407d1127 100644
--- a/Core/FileLoaders/HTTPFileLoader.cpp
+++ b/Core/FileLoaders/HTTPFileLoader.cpp
@@ -28,17 +28,20 @@ HTTPFileLoader::HTTPFileLoader(const std::string &filename)
 void HTTPFileLoader::Prepare() {
 	std::call_once(preparedFlag_, [this](){
 		if (!client_.Resolve(url_.Host().c_str(), url_.Port())) {
-			// TODO: Should probably set some flag?
+			ERROR_LOG(LOADER, "HTTP request failed, unable to resolve: %s port %d", url_.Host().c_str(), url_.Port());
 			return;
 		}
 
+		client_.SetDataTimeout(20.0);
 		Connect();
 		if (!connected_) {
+			ERROR_LOG(LOADER, "HTTP request failed, failed to connect: %s port %d", url_.Host().c_str(), url_.Port());
 			return;
 		}
 
 		int err = client_.SendRequest("HEAD", url_.Resource().c_str());
 		if (err < 0) {
+			ERROR_LOG(LOADER, "HTTP request failed, failed to send request: %s port %d", url_.Host().c_str(), url_.Port());
 			Disconnect();
 			return;
 		}
diff --git a/ext/native/base/buffer.cpp b/ext/native/base/buffer.cpp
index 9b268976bb..8e48848319 100644
--- a/ext/native/base/buffer.cpp
+++ b/ext/native/base/buffer.cpp
@@ -146,8 +146,12 @@ bool Buffer::FlushToFile(const char *filename) {
 	return true;
 }
 
-bool Buffer::FlushSocket(uintptr_t sock) {
+bool Buffer::FlushSocket(uintptr_t sock, double timeout) {
 	for (size_t pos = 0, end = data_.size(); pos < end; ) {
+		if (timeout >= 0.0 && !fd_util::WaitUntilReady(sock, timeout, true)) {
+			ELOG("FlushSocket timed out");
+			return false;
+		}
 		int sent = send(sock, &data_[pos], (int)(end - pos), MSG_NOSIGNAL);
 		if (sent < 0) {
 			ELOG("FlushSocket failed");
@@ -156,7 +160,7 @@ bool Buffer::FlushSocket(uintptr_t sock) {
 		pos += sent;
 
 		// Buffer full, don't spin.
-		if (sent == 0) {
+		if (sent == 0 && timeout < 0.0) {
 			sleep_ms(1);
 		}
 	}
diff --git a/ext/native/base/buffer.h b/ext/native/base/buffer.h
index bca84d9ba7..b34901fb17 100644
--- a/ext/native/base/buffer.h
+++ b/ext/native/base/buffer.h
@@ -59,12 +59,12 @@ class Buffer {
 
   // Simple I/O.
 
-  // Writes the entire buffer to the file descriptor. Also resets the
-  // size to zero. On failure, data remains in buffer and nothing is
-  // written.
+	// Writes the entire buffer to the file descriptor. Also resets the
+	// size to zero. On failure, data remains in buffer and nothing is
+	// written.
 	bool Flush(int fd);
 	bool FlushToFile(const char *filename);
-  bool FlushSocket(uintptr_t sock);  // Windows portability
+	bool FlushSocket(uintptr_t sock, double timeout = -1.0);  // Windows portability
 
   bool ReadAll(int fd, int hintSize = 0);
   bool ReadAllWithProgress(int fd, int knownSize, float *progress, bool *cancelled);
diff --git a/ext/native/net/http_client.cpp b/ext/native/net/http_client.cpp
index 3cb6967326..1954f69ce2 100644
--- a/ext/native/net/http_client.cpp
+++ b/ext/native/net/http_client.cpp
@@ -283,7 +283,7 @@ int Client::SendRequestWithData(const char *method, const char *resource, const
 		userAgent_,
 		otherHeaders ? otherHeaders : "");
 	buffer.Append(data);
-	bool flushed = buffer.FlushSocket(sock());
+	bool flushed = buffer.FlushSocket(sock(), dataTimeout_);
 	if (!flushed) {
 		return -1;  // TODO error code.
 	}
@@ -292,6 +292,10 @@ int Client::SendRequestWithData(const char *method, const char *resource, const
 
 int Client::ReadResponseHeaders(Buffer *readbuf, std::vector<std::string> &responseHeaders, float *progress) {
 	// Snarf all the data we can into RAM. A little unsafe but hey.
+	if (dataTimeout_ >= 0.0 && fd_util::WaitUntilReady(sock(), dataTimeout_, false)) {
+		ELOG("HTTP headers timed out");
+		return -1;
+	}
 	if (readbuf->Read(sock(), 4096) < 0) {
 		ELOG("Failed to read HTTP headers :(");
 		return -1;
diff --git a/ext/native/net/http_client.h b/ext/native/net/http_client.h
index ac3d26ed97..348cf33d93 100644
--- a/ext/native/net/http_client.h
+++ b/ext/native/net/http_client.h
@@ -75,8 +75,14 @@ public:
 	// If your response contains a response, you must read it.
 	int ReadResponseEntity(Buffer *readbuf, const std::vector<std::string> &responseHeaders, Buffer *output, float *progress = nullptr, bool *cancelled = nullptr);
 
+	void SetDataTimeout(double t) {
+		dataTimeout_ = t;
+	}
+
+protected:
 	const char *userAgent_;
 	const char *httpVersion_;
+	double dataTimeout_ = -1.0;
 };
 
 // Not particularly efficient, but hey - it's a background download, that's pretty cool :P