diff --git a/src/netops.c b/src/netops.c
index 54aaa4677..c8fe37645 100644
--- a/src/netops.c
+++ b/src/netops.c
@@ -77,7 +77,7 @@ int gitno_connect(const char *host, const char *port)
 	struct addrinfo *info, *p;
 	struct addrinfo hints;
 	int ret, error = GIT_SUCCESS;
-	int s;
+	GIT_SOCKET s;
 
 	memset(&hints, 0x0, sizeof(struct addrinfo));
 	hints.ai_family = AF_UNSPEC;
@@ -92,7 +92,11 @@ int gitno_connect(const char *host, const char *port)
 
 	for (p = info; p != NULL; p = p->ai_next) {
 		s = socket(p->ai_family, p->ai_socktype, p->ai_protocol);
+#ifdef GIT_WIN32
+		if (s == INVALID_SOCKET) {
+#else
 		if (s < 0) {
+#endif
 			error = GIT_EOSERR;
 			goto cleanup;
 		}
@@ -109,19 +113,21 @@ int gitno_connect(const char *host, const char *port)
 	}
 
 	/* Oops, we couldn't connect to any address */
-	error = GIT_EOSERR;
+	error = git__throw(GIT_EOSERR, "Failed to connect: %s", strerror(errno));
 
 cleanup:
 	freeaddrinfo(info);
 	return error;
 }
 
-int gitno_send(int s, const char *msg, size_t len, int flags)
+int gitno_send(GIT_SOCKET s, const char *msg, size_t len, int flags)
 {
 	int ret;
 	size_t off = 0;
 
 	while (off < len) {
+		errno = 0;
+
 		ret = send(s, msg + off, len - off, flags);
 		if (ret < 0)
 			return git__throw(GIT_EOSERR, "Error sending data: %s", strerror(errno));
diff --git a/src/netops.h b/src/netops.h
index 0d962ef61..b0425ae76 100644
--- a/src/netops.h
+++ b/src/netops.h
@@ -10,7 +10,7 @@
 #ifndef GIT_WIN32
 typedef int GIT_SOCKET;
 #else
-typedef unsigned int GIT_SOCKET;
+typedef SOCKET GIT_SOCKET;
 #endif
 
 typedef struct gitno_buffer {
@@ -26,7 +26,7 @@ void gitno_consume(gitno_buffer *buf, const char *ptr);
 void gitno_consume_n(gitno_buffer *buf, size_t cons);
 
 int gitno_connect(const char *host, const char *port);
-int gitno_send(int s, const char *msg, size_t len, int flags);
+int gitno_send(GIT_SOCKET s, const char *msg, size_t len, int flags);
 int gitno_select_in(gitno_buffer *buf, long int sec, long int usec);
 
 int gitno_extract_host_and_port(char **host, char **port, const char *url, const char *default_port);
diff --git a/src/transport-http.c b/src/transport-http.c
index 70086adea..3ee4025f8 100644
--- a/src/transport-http.c
+++ b/src/transport-http.c
@@ -52,6 +52,9 @@ typedef struct {
 	enum last_cb last_cb;
 	char *content_type;
 	char *service;
+#ifdef GIT_WIN32
+	WSADATA wsd;
+#endif
 } transport_http;
 
 static int gen_request(git_buf *buf, const char *url, const char *host, const char *service)
@@ -76,7 +79,8 @@ static int gen_request(git_buf *buf, const char *url, const char *host, const ch
 static int do_connect(transport_http *t, const char *service)
 {
 	git_buf request = GIT_BUF_INIT;
-	int s = -1, error;
+	int error;
+	int s;
 	const char *url, *prefix;
 	char *host = NULL, *port = NULL;
 
@@ -362,6 +366,10 @@ static int http_close(git_transport *transport)
 	if (error < 0)
 		return git__throw(GIT_EOSERR, "Failed to close the socket: %s", strerror(errno));
 
+#ifdef GIT_WIN32
+	WSACleanup();
+#endif
+
 	return GIT_SUCCESS;
 }
 
@@ -388,6 +396,9 @@ static void http_free(git_transport *transport)
 int git_transport_http(git_transport **out)
 {
 	transport_http *t;
+#ifdef GIT_WIN32
+	int ret;
+#endif
 
 	t = git__malloc(sizeof(transport_http));
 	if (t == NULL)
@@ -402,5 +413,13 @@ int git_transport_http(git_transport **out)
 
 	*out = (git_transport *) t;
 
+#ifdef GIT_WIN32
+	ret = WSAStartup(MAKEWORD(2,2), &t->wsd);
+	if (ret != 0) {
+		http_free(*out);
+		return git__throw(GIT_EOSERR, "Winsock init failed");
+	}
+#endif
+
 	return GIT_SUCCESS;
 }
diff --git a/src/transport_git.c b/src/transport_git.c
index a1c54ca83..42503e1c9 100644
--- a/src/transport_git.c
+++ b/src/transport_git.c
@@ -22,10 +22,13 @@
 
 typedef struct {
 	git_transport parent;
-	int socket;
+	GIT_SOCKET socket;
 	git_vector refs;
 	git_remote_head **heads;
 	git_transport_caps caps;
+#ifdef GIT_WIN32
+	WSADATA wsd;
+#endif
 } transport_git;
 
 /*
@@ -68,7 +71,7 @@ static int gen_proto(char **out, int *outlen, const char *cmd, const char *url)
 	return GIT_SUCCESS;
 }
 
-static int send_request(int s, const char *cmd, const char *url)
+static int send_request(GIT_SOCKET s, const char *cmd, const char *url)
 {
 	int error, len;
 	char *msg = NULL;
@@ -91,7 +94,7 @@ cleanup:
  */
 static int do_connect(transport_git *t, const char *url)
 {
-	int s = -1;
+	GIT_SOCKET s;
 	char *host, *port;
 	const char prefix[] = "git://";
 	int error, connected = 0;
@@ -525,6 +528,10 @@ static void git_free(git_transport *transport)
 		git_pkt_free(p);
 	}
 
+#ifdef GIT_WIN32
+	WSACleanup();
+#endif
+
 	git_vector_free(refs);
 	free(t->heads);
 	free(t->parent.url);
@@ -534,6 +541,9 @@ static void git_free(git_transport *transport)
 int git_transport_git(git_transport **out)
 {
 	transport_git *t;
+#ifdef GIT_WIN32
+	int ret;
+#endif
 
 	t = git__malloc(sizeof(transport_git));
 	if (t == NULL)
@@ -554,5 +564,13 @@ int git_transport_git(git_transport **out)
 
 	*out = (git_transport *) t;
 
+#ifdef GIT_WIN32
+	ret = WSAStartup(MAKEWORD(2,2), &t->wsd);
+	if (ret != 0) {
+		git_free(*out);
+		return git__throw(GIT_EOSERR, "Winsock init failed");
+	}
+#endif
+
 	return GIT_SUCCESS;
 }