thodg/libgit2

diff --git a/include/git2/remote.h b/include/git2/remote.h
index 088f528..f1aa35f 100644
--- a/include/git2/remote.h
+++ b/include/git2/remote.h
@@ -345,23 +345,6 @@ GIT_EXTERN(size_t) git_remote_refspec_count(const git_remote *remote);
 GIT_EXTERN(const git_refspec *)git_remote_get_refspec(const git_remote *remote, size_t n);
 
 /**
- * Open a connection to a remote
- *
- * The transport is selected based on the URL. The direction argument
- * is due to a limitation of the git protocol (over TCP or SSH) which
- * starts up a specific binary which can only do the one or the other.
- *
- * @param remote the remote to connect to
- * @param direction GIT_DIRECTION_FETCH if you want to fetch or
- * GIT_DIRECTION_PUSH if you want to push
- * @param callbacks the callbacks to use for this connection
- * @param proxy_opts proxy settings
- * @param custom_headers extra HTTP headers to use in this connection
- * @return 0 or an error code
- */
-GIT_EXTERN(int) git_remote_connect(git_remote *remote, git_direction direction, const git_remote_callbacks *callbacks, const git_proxy_options *proxy_opts, const git_strarray *custom_headers);
-
-/**
  * Get the remote repository's reference advertisement list
  *
  * Get the list of references with which the server responds to a new
@@ -809,7 +792,93 @@ GIT_EXTERN(int) git_push_options_init(
 	unsigned int version);
 
 /**
- * Download and index the packfile
+ * Remote creation options structure
+ *
+ * Initialize with `GIT_REMOTE_CREATE_OPTIONS_INIT`. Alternatively, you can
+ * use `git_remote_create_options_init`.
+ *
+ */
+typedef struct {
+	unsigned int version;
+
+	/** Callbacks to use for this connection */
+	git_remote_callbacks callbacks;
+
+	/** HTTP Proxy settings */
+	git_proxy_options proxy_opts;
+
+	/** Extra HTTP headers to use in this connection */
+	git_strarray custom_headers;
+} git_remote_connect_options;
+
+#define GIT_REMOTE_CONNECT_OPTIONS_VERSION 1
+#define GIT_REMOTE_CONNECT_OPTIONS_INIT { \
+	GIT_REMOTE_CONNECT_OPTIONS_VERSION, \
+	GIT_REMOTE_CALLBACKS_INIT, \
+	GIT_PROXY_OPTIONS_INIT }
+
+/**
+ * Initialize git_remote_connect_options structure.
+ *
+ * Initializes a `git_remote_connect_options` with default values.
+ * Equivalent to creating an instance with
+ * `GIT_REMOTE_CONNECT_OPTIONS_INIT`.
+ *
+ * @param opts The `git_remote_connect_options` struct to initialize.
+ * @param version The struct version; pass `GIT_REMOTE_CONNECT_OPTIONS_VERSION`.
+ * @return Zero on success; -1 on failure.
+ */
+GIT_EXTERN(int) git_remote_connect_options_init(
+		git_remote_connect_options *opts,
+		unsigned int version);
+
+/**
+ * Open a connection to a remote.
+ *
+ * The transport is selected based on the URL; the direction argument
+ * is due to a limitation of the git protocol which starts up a
+ * specific binary which can only do the one or the other.
+ *
+ * @param remote the remote to connect to
+ * @param direction GIT_DIRECTION_FETCH if you want to fetch or
+ * GIT_DIRECTION_PUSH if you want to push
+ * @param callbacks the callbacks to use for this connection
+ * @param proxy_opts proxy settings
+ * @param custom_headers extra HTTP headers to use in this connection
+ * @return 0 or an error code
+ */
+GIT_EXTERN(int) git_remote_connect(
+	git_remote *remote,
+	git_direction direction,
+	const git_remote_callbacks *callbacks,
+	const git_proxy_options *proxy_opts,
+	const git_strarray *custom_headers);
+
+/**
+ * Open a connection to a remote with extended options.
+ *
+ * The transport is selected based on the URL; the direction argument
+ * is due to a limitation of the git protocol which starts up a
+ * specific binary which can only do the one or the other.
+ *
+ * The given options structure will form the defaults for connection
+ * options and callback setup.  Callers may override these defaults
+ * by specifying `git_fetch_options` or `git_push_options` in
+ * subsequent calls.
+ *
+ * @param remote the remote to connect to
+ * @param direction GIT_DIRECTION_FETCH if you want to fetch or
+ * GIT_DIRECTION_PUSH if you want to push
+ * @param opts the remote connection options
+ * @return 0 or an error code
+ */
+GIT_EXTERN(int) git_remote_connect_ext(
+	git_remote *remote,
+	git_direction direction,
+	const git_remote_connect_options *opts);
+
+/**
+ * Download and index the packfile.
  *
  * Connect to the remote if it hasn't been done yet, negotiate with
  * the remote git which objects are missing, download and index the
@@ -818,19 +887,31 @@ GIT_EXTERN(int) git_push_options_init(
  * The .idx file will be created and both it and the packfile with be
  * renamed to their final name.
  *
+ * If options are specified and this remote is already connected then
+ * the existing remote connection options will be discarded and the
+ * remote will now use the new options.
+ *
  * @param remote the remote
  * @param refspecs the refspecs to use for this negotiation and
  * download. Use NULL or an empty array to use the base refspecs
- * @param opts the options to use for this fetch
+ * @param opts the options to use for this fetch or NULL
  * @return 0 or an error code
  */
- GIT_EXTERN(int) git_remote_download(git_remote *remote, const git_strarray *refspecs, const git_fetch_options *opts);
+ GIT_EXTERN(int) git_remote_download(
+	git_remote *remote,
+	const git_strarray *refspecs,
+	const git_fetch_options *opts);
 
 /**
  * Create a packfile and send it to the server
  *
  * Connect to the remote if it hasn't been done yet, negotiate with
- * the remote git which objects are missing, create a packfile with the missing objects and send it.
+ * the remote git which objects are missing, create a packfile with
+ * the missing objects and send it.
+ *
+ * If options are specified and this remote is already connected then
+ * the existing remote connection options will be discarded and the
+ * remote will now use the new options.
  *
  * @param remote the remote
  * @param refspecs the refspecs to use for this negotiation and
@@ -838,17 +919,23 @@ GIT_EXTERN(int) git_push_options_init(
  * @param opts the options to use for this push
  * @return 0 or an error code
  */
-GIT_EXTERN(int) git_remote_upload(git_remote *remote, const git_strarray *refspecs, const git_push_options *opts);
+GIT_EXTERN(int) git_remote_upload(
+	git_remote *remote,
+	const git_strarray *refspecs,
+	const git_push_options *opts);
 
 /**
- * Update the tips to the new state
+ * Update the tips to the new state.
+ *
+ * If callbacks are not specified then the callbacks specified to
+ * `git_remote_connect` will be used (if it was called).
  *
  * @param remote the remote to update
  * @param reflog_message The message to insert into the reflogs. If
  * NULL and fetching, the default is "fetch <name>", where <name> is
  * the name of the remote (or its url, for in-memory remotes). This
  * parameter is ignored when pushing.
- * @param callbacks  pointer to the callback structure to use
+ * @param callbacks  pointer to the callback structure to use or NULL
  * @param update_fetchhead whether to write to FETCH_HEAD. Pass 1 to behave like git.
  * @param download_tags what the behaviour for downloading tags is for this fetch. This is
  * ignored for push. This must be the same value passed to `git_remote_download()`.
@@ -862,15 +949,19 @@ GIT_EXTERN(int) git_remote_update_tips(
 		const char *reflog_message);
 
 /**
- * Download new data and update tips
+ * Download new data and update tips.
  *
  * Convenience function to connect to a remote, download the data,
  * disconnect and update the remote-tracking branches.
  *
+ * If options are specified and this remote is already connected then
+ * the existing remote connection options will be discarded and the
+ * remote will now use the new options.
+ *
  * @param remote the remote to fetch from
  * @param refspecs the refspecs to use for this fetch. Pass NULL or an
  *                 empty array to use the base refspecs.
- * @param opts options to use for this fetch
+ * @param opts options to use for this fetch or NULL
  * @param reflog_message The message to insert into the reflogs. If NULL, the
  *								 default is "fetch"
  * @return 0 or an error code
@@ -882,27 +973,35 @@ GIT_EXTERN(int) git_remote_fetch(
 		const char *reflog_message);
 
 /**
- * Prune tracking refs that are no longer present on remote
+ * Prune tracking refs that are no longer present on remote.
+ *
+ * If callbacks are not specified then the callbacks specified to
+ * `git_remote_connect` will be used (if it was called).
  *
  * @param remote the remote to prune
  * @param callbacks callbacks to use for this prune
  * @return 0 or an error code
  */
-GIT_EXTERN(int) git_remote_prune(git_remote *remote, const git_remote_callbacks *callbacks);
+GIT_EXTERN(int) git_remote_prune(
+	git_remote *remote,
+	const git_remote_callbacks *callbacks);
 
 /**
- * Perform a push
+ * Perform a push.
  *
- * Peform all the steps from a push.
+ * If options are specified and this remote is already connected then
+ * the existing remote connection options will be discarded and the
+ * remote will now use the new options.
  *
  * @param remote the remote to push to
  * @param refspecs the refspecs to use for pushing. If NULL or an empty
  *                 array, the configured refspecs will be used
  * @param opts options to use for this push
  */
-GIT_EXTERN(int) git_remote_push(git_remote *remote,
-				const git_strarray *refspecs,
-				const git_push_options *opts);
+GIT_EXTERN(int) git_remote_push(
+	git_remote *remote,
+	const git_strarray *refspecs,
+	const git_push_options *opts);
 
 /**
  * Get the statistics structure that is filled in by the fetch operation.
diff --git a/include/git2/sys/transport.h b/include/git2/sys/transport.h
index 76003ee..89e6876 100644
--- a/include/git2/sys/transport.h
+++ b/include/git2/sys/transport.h
@@ -24,31 +24,9 @@
 
 GIT_BEGIN_DECL
 
-/**
- * Flags to pass to transport
- *
- * Currently unused.
- */
-typedef enum {
-	GIT_TRANSPORTFLAGS_NONE = 0
-} git_transport_flags_t;
-
 struct git_transport {
 	unsigned int version; /**< The struct version */
 
-	/** Set progress and error callbacks */
-	int GIT_CALLBACK(set_callbacks)(
-		git_transport *transport,
-		git_transport_message_cb progress_cb,
-		git_transport_message_cb error_cb,
-		git_transport_certificate_check_cb certificate_check_cb,
-		void *payload);
-
-	/** Set custom headers for HTTP requests */
-	int GIT_CALLBACK(set_custom_headers)(
-		git_transport *transport,
-		const git_strarray *custom_headers);
-
 	/**
 	 * Connect the transport to the remote repository, using the given
 	 * direction.
@@ -56,11 +34,17 @@ struct git_transport {
 	int GIT_CALLBACK(connect)(
 		git_transport *transport,
 		const char *url,
-		git_credential_acquire_cb cred_acquire_cb,
-		void *cred_acquire_payload,
-		const git_proxy_options *proxy_opts,
 		int direction,
-		int flags);
+		const git_remote_connect_options *connect_opts);
+
+	/**
+	 * Resets the connect options for the given transport.  This
+	 * is useful for updating settings or callbacks for an already
+	 * connected transport.
+	 */
+	int GIT_CALLBACK(set_connect_opts)(
+		git_transport *transport,
+		const git_remote_connect_options *connect_opts);
 
 	/**
 	 * Get the list of available references in the remote repository.
@@ -75,7 +59,9 @@ struct git_transport {
 		git_transport *transport);
 
 	/** Executes the push whose context is in the git_push object. */
-	int GIT_CALLBACK(push)(git_transport *transport, git_push *push, const git_remote_callbacks *callbacks);
+	int GIT_CALLBACK(push)(
+		git_transport *transport,
+		git_push *push);
 
 	/**
 	 * Negotiate a fetch with the remote repository.
@@ -99,16 +85,11 @@ struct git_transport {
 	int GIT_CALLBACK(download_pack)(
 		git_transport *transport,
 		git_repository *repo,
-		git_indexer_progress *stats,
-		git_indexer_progress_cb progress_cb,
-		void *progress_payload);
+		git_indexer_progress *stats);
 
 	/** Checks to see if the transport is connected */
 	int GIT_CALLBACK(is_connected)(git_transport *transport);
 
-	/** Reads the flags value previously passed into connect() */
-	int GIT_CALLBACK(read_flags)(git_transport *transport, int *flags);
-
 	/** Cancels any outstanding transport operation */
 	void GIT_CALLBACK(cancel)(git_transport *transport);
 
diff --git a/src/fetch.c b/src/fetch.c
index bc5961d..117c8f2 100644
--- a/src/fetch.c
+++ b/src/fetch.c
@@ -134,21 +134,14 @@ int git_fetch_negotiate(git_remote *remote, const git_fetch_options *opts)
 		remote->refs.length);
 }
 
-int git_fetch_download_pack(git_remote *remote, const git_remote_callbacks *callbacks)
+int git_fetch_download_pack(git_remote *remote)
 {
 	git_transport *t = remote->transport;
-	git_indexer_progress_cb progress = NULL;
-	void *payload = NULL;
 
 	if (!remote->need_pack)
 		return 0;
 
-	if (callbacks) {
-		progress = callbacks->transfer_progress;
-		payload  = callbacks->payload;
-	}
-
-	return t->download_pack(t, remote->repo, &remote->stats, progress, payload);
+	return t->download_pack(t, remote->repo, &remote->stats);
 }
 
 int git_fetch_options_init(git_fetch_options *opts, unsigned int version)
diff --git a/src/fetch.h b/src/fetch.h
index 1c75af9..10b6731 100644
--- a/src/fetch.h
+++ b/src/fetch.h
@@ -15,7 +15,7 @@
 
 int git_fetch_negotiate(git_remote *remote, const git_fetch_options *opts);
 
-int git_fetch_download_pack(git_remote *remote, const git_remote_callbacks *callbacks);
+int git_fetch_download_pack(git_remote *remote);
 
 int git_fetch_setup_walk(git_revwalk **out, git_repository *repo);
 
diff --git a/src/proxy.c b/src/proxy.c
index 78a4c55..ef91ad6 100644
--- a/src/proxy.c
+++ b/src/proxy.c
@@ -39,8 +39,11 @@ int git_proxy_options_dup(git_proxy_options *tgt, const git_proxy_options *src)
 	return 0;
 }
 
-void git_proxy_options_clear(git_proxy_options *opts)
+void git_proxy_options_dispose(git_proxy_options *opts)
 {
+	if (!opts)
+		return;
+
 	git__free((char *) opts->url);
 	opts->url = NULL;
 }
diff --git a/src/proxy.h b/src/proxy.h
index f8b5c4b..7c0ab59 100644
--- a/src/proxy.h
+++ b/src/proxy.h
@@ -12,6 +12,6 @@
 #include "git2/proxy.h"
 
 extern int git_proxy_options_dup(git_proxy_options *tgt, const git_proxy_options *src);
-extern void git_proxy_options_clear(git_proxy_options *opts);
+extern void git_proxy_options_dispose(git_proxy_options *opts);
 
 #endif
diff --git a/src/push.c b/src/push.c
index 9733eec..da8aeba 100644
--- a/src/push.c
+++ b/src/push.c
@@ -29,19 +29,26 @@ static int push_status_ref_cmp(const void *a, const void *b)
 	return strcmp(push_status_a->ref, push_status_b->ref);
 }
 
-int git_push_new(git_push **out, git_remote *remote)
+int git_push_new(git_push **out, git_remote *remote, const git_push_options *opts)
 {
 	git_push *p;
 
 	*out = NULL;
 
+	GIT_ERROR_CHECK_VERSION(opts, GIT_PUSH_OPTIONS_VERSION, "git_push_options");
+
 	p = git__calloc(1, sizeof(*p));
 	GIT_ERROR_CHECK_ALLOC(p);
 
 	p->repo = remote->repo;
 	p->remote = remote;
 	p->report_status = 1;
-	p->pb_parallelism = 1;
+	p->pb_parallelism = opts ? opts->pb_parallelism : 1;
+
+	if (opts) {
+		GIT_ERROR_CHECK_VERSION(&opts->callbacks, GIT_REMOTE_CALLBACKS_VERSION, "git_remote_callbacks");
+		memcpy(&p->callbacks, &opts->callbacks, sizeof(git_remote_callbacks));
+	}
 
 	if (git_vector_init(&p->specs, 0, push_spec_rref_cmp) < 0) {
 		git__free(p);
@@ -65,20 +72,6 @@ int git_push_new(git_push **out, git_remote *remote)
 	return 0;
 }
 
-int git_push_set_options(git_push *push, const git_push_options *opts)
-{
-	if (!push || !opts)
-		return -1;
-
-	GIT_ERROR_CHECK_VERSION(opts, GIT_PUSH_OPTIONS_VERSION, "git_push_options");
-
-	push->pb_parallelism = opts->pb_parallelism;
-	push->connection.custom_headers = &opts->custom_headers;
-	push->connection.proxy = &opts->proxy_opts;
-
-	return 0;
-}
-
 static void free_refspec(push_spec *spec)
 {
 	if (spec == NULL)
@@ -411,10 +404,11 @@ static int calculate_work(git_push *push)
 	return 0;
 }
 
-static int do_push(git_push *push, const git_remote_callbacks *callbacks)
+static int do_push(git_push *push)
 {
 	int error = 0;
 	git_transport *transport = push->remote->transport;
+	git_remote_callbacks *callbacks = &push->callbacks;
 
 	if (!transport->push) {
 		git_error_set(GIT_ERROR_NET, "remote transport doesn't support push");
@@ -446,7 +440,7 @@ static int do_push(git_push *push, const git_remote_callbacks *callbacks)
 	    goto on_error;
 
 	if ((error = queue_objects(push)) < 0 ||
-	    (error = transport->push(transport, push, callbacks)) < 0)
+	    (error = transport->push(transport, push)) < 0)
 		goto on_error;
 
 on_error:
@@ -472,7 +466,7 @@ static int filter_refs(git_remote *remote)
 	return 0;
 }
 
-int git_push_finish(git_push *push, const git_remote_callbacks *callbacks)
+int git_push_finish(git_push *push)
 {
 	int error;
 
@@ -482,7 +476,7 @@ int git_push_finish(git_push *push, const git_remote_callbacks *callbacks)
 	}
 
 	if ((error = filter_refs(push->remote)) < 0 ||
-	    (error = do_push(push, callbacks)) < 0)
+	    (error = do_push(push)) < 0)
 		return error;
 
 	if (!push->unpack_ok) {
diff --git a/src/push.h b/src/push.h
index 8675639..fc72e84 100644
--- a/src/push.h
+++ b/src/push.h
@@ -41,7 +41,7 @@ struct git_push {
 
 	/* options */
 	unsigned pb_parallelism;
-	git_remote_connection_opts connection;
+	git_remote_callbacks callbacks;
 };
 
 /**
@@ -56,22 +56,11 @@ void git_push_status_free(push_status *status);
  *
  * @param out New push object
  * @param remote Remote instance
+ * @param opts Push options or NULL
  *
  * @return 0 or an error code
  */
-int git_push_new(git_push **out, git_remote *remote);
-
-/**
- * Set options on a push object
- *
- * @param push The push object
- * @param opts The options to set on the push object
- *
- * @return 0 or an error code
- */
-int git_push_set_options(
-	git_push *push,
-	const git_push_options *opts);
+int git_push_new(git_push **out, git_remote *remote, const git_push_options *opts);
 
 /**
  * Add a refspec to be pushed
@@ -104,11 +93,10 @@ int git_push_update_tips(git_push *push, const git_remote_callbacks *callbacks);
  * order to find out which updates were accepted or rejected.
  *
  * @param push The push object
- * @param callbacks the callbacks to use for this connection
  *
  * @return 0 or an error code
  */
-int git_push_finish(git_push *push, const git_remote_callbacks *callbacks);
+int git_push_finish(git_push *push);
 
 /**
  * Invoke callback `cb' on each status entry
diff --git a/src/remote.c b/src/remote.c
index f697e0f..208d8d0 100644
--- a/src/remote.c
+++ b/src/remote.c
@@ -16,6 +16,7 @@
 #include "refspec.h"
 #include "fetchhead.h"
 #include "push.h"
+#include "proxy.h"
 
 #include "git2/config.h"
 #include "git2/types.h"
@@ -756,54 +757,155 @@ int git_remote__urlfordirection(
 	return resolve_url(url_out, url, direction, callbacks);
 }
 
-static int remote_transport_set_callbacks(git_transport *t, const git_remote_callbacks *cbs)
+int git_remote_connect_options_init(
+	git_remote_connect_options *opts,
+	unsigned int version)
 {
-	if (!t->set_callbacks || !cbs)
+	GIT_INIT_STRUCTURE_FROM_TEMPLATE(
+		opts, version, git_remote_connect_options, GIT_REMOTE_CONNECT_OPTIONS_INIT);
+	return 0;
+}
+
+int git_remote_connect_options_dup(
+	git_remote_connect_options *dst,
+	const git_remote_connect_options *src)
+{
+	memcpy(dst, src, sizeof(git_remote_connect_options));
+
+	if (git_proxy_options_dup(&dst->proxy_opts, &src->proxy_opts) < 0 ||
+	    git_strarray_copy(&dst->custom_headers, &src->custom_headers) < 0)
+		return -1;
+
+	return 0;
+}
+
+void git_remote_connect_options_dispose(git_remote_connect_options *opts)
+{
+	if (!opts)
+		return;
+
+	git_strarray_dispose(&opts->custom_headers);
+	git_proxy_options_dispose(&opts->proxy_opts);
+}
+
+static size_t http_header_name_length(const char *http_header)
+{
+	const char *colon = strchr(http_header, ':');
+	if (!colon)
+		return 0;
+	return colon - http_header;
+}
+
+static bool is_malformed_http_header(const char *http_header)
+{
+	const char *c;
+	size_t name_len;
+
+	/* Disallow \r and \n */
+	if ((c = strchr(http_header, '\r')) != NULL)
+		return true;
+	if ((c = strchr(http_header, '\n')) != NULL)
+		return true;
+
+	/* Require a header name followed by : */
+	if ((name_len = http_header_name_length(http_header)) < 1)
+		return true;
+
+	return false;
+}
+
+static char *forbidden_custom_headers[] = {
+	"User-Agent",
+	"Host",
+	"Accept",
+	"Content-Type",
+	"Transfer-Encoding",
+	"Content-Length",
+};
+
+static bool is_forbidden_custom_header(const char *custom_header)
+{
+	unsigned long i;
+	size_t name_len = http_header_name_length(custom_header);
+
+	/* Disallow headers that we set */
+	for (i = 0; i < ARRAY_SIZE(forbidden_custom_headers); i++)
+		if (strncmp(forbidden_custom_headers[i], custom_header, name_len) == 0)
+			return true;
+
+	return false;
+}
+
+static int validate_custom_headers(const git_strarray *custom_headers)
+{
+	size_t i;
+
+	if (!custom_headers)
 		return 0;
 
-	return t->set_callbacks(t, cbs->sideband_progress, NULL,
-				cbs->certificate_check, cbs->payload);
+	for (i = 0; i < custom_headers->count; i++) {
+		if (is_malformed_http_header(custom_headers->strings[i])) {
+			git_error_set(GIT_ERROR_INVALID, "custom HTTP header '%s' is malformed", custom_headers->strings[i]);
+			return -1;
+		}
+
+		if (is_forbidden_custom_header(custom_headers->strings[i])) {
+			git_error_set(GIT_ERROR_INVALID, "custom HTTP header '%s' is already set by libgit2", custom_headers->strings[i]);
+			return -1;
+		}
+	}
+
+	return 0;
 }
 
-static int set_transport_custom_headers(git_transport *t, const git_strarray *custom_headers)
+int git_remote_connect_options_normalize(
+	git_remote_connect_options *dst,
+	const git_remote_connect_options *src)
 {
-	if (!t->set_custom_headers)
+	git_remote_connect_options_dispose(dst);
+
+	if (!src) {
+		git_remote_connect_options_init(dst, GIT_REMOTE_CONNECT_OPTIONS_VERSION);
 		return 0;
+	}
+
+	GIT_ERROR_CHECK_VERSION(src, GIT_REMOTE_CONNECT_OPTIONS_VERSION, "git_remote_connect_options");
+	GIT_ERROR_CHECK_VERSION(&src->callbacks, GIT_REMOTE_CALLBACKS_VERSION, "git_remote_callbacks");
+	GIT_ERROR_CHECK_VERSION(&src->proxy_opts, GIT_PROXY_OPTIONS_VERSION, "git_proxy_options");
 
-	return t->set_custom_headers(t, custom_headers);
+	if (validate_custom_headers(&src->custom_headers))
+		return -1;
+
+	return git_remote_connect_options_dup(dst, src);
 }
 
-int git_remote__connect(git_remote *remote, git_direction direction, const git_remote_callbacks *callbacks, const git_remote_connection_opts *conn)
+int git_remote_connect_ext(
+	git_remote *remote,
+	git_direction direction,
+	const git_remote_connect_options *given_opts)
 {
-	git_transport *t;
+	git_remote_connect_options opts = GIT_REMOTE_CONNECT_OPTIONS_INIT;
 	git_str url = GIT_STR_INIT;
-	int flags = GIT_TRANSPORTFLAGS_NONE;
+	git_transport *t;
 	int error;
-	void *payload = NULL;
-	git_credential_acquire_cb credentials = NULL;
-	git_transport_cb transport = NULL;
 
 	GIT_ASSERT_ARG(remote);
 
-	if (callbacks) {
-		GIT_ERROR_CHECK_VERSION(callbacks, GIT_REMOTE_CALLBACKS_VERSION, "git_remote_callbacks");
-		credentials = callbacks->credentials;
-		transport   = callbacks->transport;
-		payload     = callbacks->payload;
-	}
+	if (given_opts)
+		memcpy(&opts, given_opts, sizeof(git_remote_connect_options));
 
-	if (conn->proxy)
-		GIT_ERROR_CHECK_VERSION(conn->proxy, GIT_PROXY_OPTIONS_VERSION, "git_proxy_options");
+	GIT_ERROR_CHECK_VERSION(&opts.callbacks, GIT_REMOTE_CALLBACKS_VERSION, "git_remote_callbacks");
+	GIT_ERROR_CHECK_VERSION(&opts.proxy_opts, GIT_PROXY_OPTIONS_VERSION, "git_proxy_options");
 
 	t = remote->transport;
 
-	if ((error = git_remote__urlfordirection(&url, remote, direction, callbacks)) < 0)
+	if ((error = git_remote__urlfordirection(&url, remote, direction, &opts.callbacks)) < 0)
 		goto on_error;
 
 	/* If we don't have a transport object yet, and the caller specified a
 	 * custom transport factory, use that */
-	if (!t && transport &&
-		(error = transport(&t, remote, payload)) < 0)
+	if (!t && opts.callbacks.transport &&
+	    (error = opts.callbacks.transport(&t, remote, opts.callbacks.payload)) < 0)
 		goto on_error;
 
 	/* If we still don't have a transport, then use the global
@@ -811,11 +913,7 @@ int git_remote__connect(git_remote *remote, git_direction direction, const git_r
 	if (!t && (error = git_transport_new(&t, remote, url.ptr)) < 0)
 		goto on_error;
 
-	if ((error = set_transport_custom_headers(t, conn->custom_headers)) != 0)
-		goto on_error;
-
-	if ((error = remote_transport_set_callbacks(t, callbacks)) < 0 ||
-	    (error = t->connect(t, url.ptr, credentials, payload, conn->proxy, direction, flags)) != 0)
+	if ((error = t->connect(t, url.ptr, direction, &opts)) != 0)
 		goto on_error;
 
 	remote->transport = t;
@@ -836,14 +934,25 @@ on_error:
 	return error;
 }
 
-int git_remote_connect(git_remote *remote, git_direction direction, const git_remote_callbacks *callbacks, const git_proxy_options *proxy, const git_strarray *custom_headers)
+int git_remote_connect(
+	git_remote *remote,
+	git_direction direction,
+	const git_remote_callbacks *callbacks,
+	const git_proxy_options *proxy,
+	const git_strarray *custom_headers)
 {
-	git_remote_connection_opts conn;
+	git_remote_connect_options opts = GIT_REMOTE_CONNECT_OPTIONS_INIT;
+
+	if (callbacks)
+		memcpy(&opts.callbacks, callbacks, sizeof(git_remote_callbacks));
 
-	conn.proxy = proxy;
-	conn.custom_headers = custom_headers;
+	if (proxy)
+		memcpy(&opts.proxy_opts, proxy, sizeof(git_proxy_options));
 
-	return git_remote__connect(remote, direction, callbacks, &conn);
+	if (custom_headers)
+		memcpy(&opts.custom_headers, custom_headers, sizeof(git_strarray));
+
+	return git_remote_connect_ext(remote, direction, &opts);
 }
 
 int git_remote_ls(const git_remote_head ***out, size_t *size, git_remote *remote)
@@ -1057,33 +1166,43 @@ static int ls_to_vector(git_vector *out, git_remote *remote)
 	return 0;
 }
 
-int git_remote_download(git_remote *remote, const git_strarray *refspecs, const git_fetch_options *opts)
-{
-	int error = -1;
-	size_t i;
-	git_vector *to_active, specs = GIT_VECTOR_INIT, refs = GIT_VECTOR_INIT;
-	const git_remote_callbacks *cbs = NULL;
-	const git_strarray *custom_headers = NULL;
-	const git_proxy_options *proxy = NULL;
-
-	GIT_ASSERT_ARG(remote);
-
-	if (!remote->repo) {
-		git_error_set(GIT_ERROR_INVALID, "cannot download detached remote");
-		return -1;
+#define copy_opts(out, in) \
+	if (in) { \
+		(out)->callbacks = (in)->callbacks; \
+		(out)->proxy_opts = (in)->proxy_opts; \
+		(out)->custom_headers = (in)->custom_headers; \
 	}
 
-	if (opts) {
-		GIT_ERROR_CHECK_VERSION(&opts->callbacks, GIT_REMOTE_CALLBACKS_VERSION, "git_remote_callbacks");
-		cbs = &opts->callbacks;
-		custom_headers = &opts->custom_headers;
-		GIT_ERROR_CHECK_VERSION(&opts->proxy_opts, GIT_PROXY_OPTIONS_VERSION, "git_proxy_options");
-		proxy = &opts->proxy_opts;
+GIT_INLINE(int) connect_opts_from_fetch_opts(
+	git_remote_connect_options *out,
+	const git_fetch_options *fetch_opts)
+{
+	git_remote_connect_options tmp = GIT_REMOTE_CONNECT_OPTIONS_INIT;
+	copy_opts(&tmp, fetch_opts);
+	return git_remote_connect_options_normalize(out, &tmp);
+}
+
+static int connect_or_reset_options(
+	git_remote *remote,
+	int direction,
+	git_remote_connect_options *opts)
+{
+	if (!git_remote_connected(remote)) {
+		return git_remote_connect_ext(remote, direction, opts);
+	} else {
+		return remote->transport->set_connect_opts(remote->transport, opts);
 	}
+}
 
-	if (!git_remote_connected(remote) &&
-	    (error = git_remote_connect(remote, GIT_DIRECTION_FETCH, cbs, proxy, custom_headers)) < 0)
-		goto on_error;
+/* Download from an already connected remote. */
+static int git_remote__download(
+	git_remote *remote,
+	const git_strarray *refspecs,
+	const git_fetch_options *opts)
+{
+	git_vector *to_active, specs = GIT_VECTOR_INIT, refs = GIT_VECTOR_INIT;
+	size_t i;
+	int error;
 
 	if (ls_to_vector(&refs, remote) < 0)
 		return -1;
@@ -1116,7 +1235,7 @@ int git_remote_download(git_remote *remote, const git_strarray *refspecs, const 
 	git_vector_free(&specs);
 
 	if (error < 0)
-		return error;
+		goto on_error;
 
 	if (remote->push) {
 		git_push_free(remote->push);
@@ -1124,9 +1243,9 @@ int git_remote_download(git_remote *remote, const git_strarray *refspecs, const 
 	}
 
 	if ((error = git_fetch_negotiate(remote, opts)) < 0)
-		return error;
+		goto on_error;
 
-	return git_fetch_download_pack(remote, cbs);
+	error = git_fetch_download_pack(remote);
 
 on_error:
 	git_vector_free(&refs);
@@ -1135,41 +1254,69 @@ on_error:
 	return error;
 }
 
+int git_remote_download(
+	git_remote *remote,
+	const git_strarray *refspecs,
+	const git_fetch_options *opts)
+{
+	git_remote_connect_options connect_opts = GIT_REMOTE_CONNECT_OPTIONS_INIT;
+	int error;
+
+	GIT_ASSERT_ARG(remote);
+
+	if (!remote->repo) {
+		git_error_set(GIT_ERROR_INVALID, "cannot download detached remote");
+		return -1;
+	}
+
+	if (connect_opts_from_fetch_opts(&connect_opts, opts) < 0)
+		return -1;
+
+	if ((error = connect_or_reset_options(remote, GIT_DIRECTION_FETCH, &connect_opts)) < 0)
+		return error;
+
+	return git_remote__download(remote, refspecs, opts);
+}
+
 int git_remote_fetch(
-		git_remote *remote,
-		const git_strarray *refspecs,
-		const git_fetch_options *opts,
-		const char *reflog_message)
+	git_remote *remote,
+	const git_strarray *refspecs,
+	const git_fetch_options *opts,
+	const char *reflog_message)
 {
 	int error, update_fetchhead = 1;
 	git_remote_autotag_option_t tagopt = remote->download_tags;
 	bool prune = false;
 	git_str reflog_msg_buf = GIT_STR_INIT;
-	const git_remote_callbacks *cbs = NULL;
-	git_remote_connection_opts conn = GIT_REMOTE_CONNECTION_OPTIONS_INIT;
+	git_remote_connect_options connect_opts = GIT_REMOTE_CONNECT_OPTIONS_INIT;
+
+	GIT_ASSERT_ARG(remote);
+
+	if (!remote->repo) {
+		git_error_set(GIT_ERROR_INVALID, "cannot download detached remote");
+		return -1;
+	}
+
+	if (connect_opts_from_fetch_opts(&connect_opts, opts) < 0)
+		return -1;
+
+	if ((error = connect_or_reset_options(remote, GIT_DIRECTION_FETCH, &connect_opts)) < 0)
+		return error;
 
 	if (opts) {
-		GIT_ERROR_CHECK_VERSION(&opts->callbacks, GIT_REMOTE_CALLBACKS_VERSION, "git_remote_callbacks");
-		cbs = &opts->callbacks;
-		conn.custom_headers = &opts->custom_headers;
 		update_fetchhead = opts->update_fetchhead;
 		tagopt = opts->download_tags;
-		GIT_ERROR_CHECK_VERSION(&opts->proxy_opts, GIT_PROXY_OPTIONS_VERSION, "git_proxy_options");
-		conn.proxy = &opts->proxy_opts;
 	}
 
 	/* Connect and download everything */
-	if ((error = git_remote__connect(remote, GIT_DIRECTION_FETCH, cbs, &conn)) != 0)
-		return error;
-
-	error = git_remote_download(remote, refspecs, opts);
+	error = git_remote__download(remote, refspecs, opts);
 
 	/* We don't need to be connected anymore */
 	git_remote_disconnect(remote);
 
 	/* If the download failed, return the error */
 	if (error != 0)
-		return error;
+		goto done;
 
 	/* Default reflog message */
 	if (reflog_message)
@@ -1180,10 +1327,10 @@ int git_remote_fetch(
 	}
 
 	/* Create "remote/foo" branches for all remote branches */
-	error = git_remote_update_tips(remote, cbs, update_fetchhead, tagopt, git_str_cstr(&reflog_msg_buf));
+	error = git_remote_update_tips(remote, &connect_opts.callbacks, update_fetchhead, tagopt, git_str_cstr(&reflog_msg_buf));
 	git_str_dispose(&reflog_msg_buf);
 	if (error < 0)
-		return error;
+		goto done;
 
 	if (opts && opts->prune == GIT_FETCH_PRUNE)
 		prune = true;
@@ -1195,8 +1342,10 @@ int git_remote_fetch(
 		prune = remote->prune_refs;
 
 	if (prune)
-		error = git_remote_prune(remote, cbs);
+		error = git_remote_prune(remote, &connect_opts.callbacks);
 
+done:
+	git_remote_connect_options_dispose(&connect_opts);
 	return error;
 }
 
@@ -2619,14 +2768,25 @@ done:
 	return error;
 }
 
-int git_remote_upload(git_remote *remote, const git_strarray *refspecs, const git_push_options *opts)
+GIT_INLINE(int) connect_opts_from_push_opts(
+	git_remote_connect_options *out,
+	const git_push_options *push_opts)
 {
-	size_t i;
-	int error;
+	git_remote_connect_options tmp = GIT_REMOTE_CONNECT_OPTIONS_INIT;
+	copy_opts(&tmp, push_opts);
+	return git_remote_connect_options_normalize(out, &tmp);
+}
+
+int git_remote_upload(
+	git_remote *remote,
+	const git_strarray *refspecs,
+	const git_push_options *opts)
+{
+	git_remote_connect_options connect_opts = GIT_REMOTE_CONNECT_OPTIONS_INIT;
 	git_push *push;
 	git_refspec *spec;
-	const git_remote_callbacks *cbs = NULL;
-	git_remote_connection_opts conn = GIT_REMOTE_CONNECTION_OPTIONS_INIT;
+	size_t i;
+	int error;
 
 	GIT_ASSERT_ARG(remote);
 
@@ -2635,14 +2795,10 @@ int git_remote_upload(git_remote *remote, const git_strarray *refspecs, const gi
 		return -1;
 	}
 
-	if (opts) {
-		cbs = &opts->callbacks;
-		conn.custom_headers = &opts->custom_headers;
-		conn.proxy = &opts->proxy_opts;
-	}
+	if ((error = connect_opts_from_push_opts(&connect_opts, opts)) < 0)
+		goto cleanup;
 
-	if (!git_remote_connected(remote) &&
-	    (error = git_remote__connect(remote, GIT_DIRECTION_PUSH, cbs, &conn)) < 0)
+	if ((error = connect_or_reset_options(remote, GIT_DIRECTION_PUSH, &connect_opts)) < 0)
 		goto cleanup;
 
 	free_refspecs(&remote->active_refspecs);
@@ -2654,14 +2810,11 @@ int git_remote_upload(git_remote *remote, const git_strarray *refspecs, const gi
 		remote->push = NULL;
 	}
 
-	if ((error = git_push_new(&remote->push, remote)) < 0)
-		return error;
+	if ((error = git_push_new(&remote->push, remote, opts)) < 0)
+		goto cleanup;
 
 	push = remote->push;
 
-	if (opts && (error = git_push_set_options(push, opts)) < 0)
-		goto cleanup;
-
 	if (refspecs && refspecs->count > 0) {
 		for (i = 0; i < refspecs->count; i++) {
 			if ((error = git_push_add_refspec(push, refspecs->strings[i])) < 0)
@@ -2676,23 +2829,25 @@ int git_remote_upload(git_remote *remote, const git_strarray *refspecs, const gi
 		}
 	}
 
-	if ((error = git_push_finish(push, cbs)) < 0)
+	if ((error = git_push_finish(push)) < 0)
 		goto cleanup;
 
-	if (cbs && cbs->push_update_reference &&
-	    (error = git_push_status_foreach(push, cbs->push_update_reference, cbs->payload)) < 0)
+	if (connect_opts.callbacks.push_update_reference &&
+	    (error = git_push_status_foreach(push, connect_opts.callbacks.push_update_reference, connect_opts.callbacks.payload)) < 0)
 		goto cleanup;
 
 cleanup:
+	git_remote_connect_options_dispose(&connect_opts);
 	return error;
 }
 
-int git_remote_push(git_remote *remote, const git_strarray *refspecs, const git_push_options *opts)
+int git_remote_push(
+	git_remote *remote,
+	const git_strarray *refspecs,
+	const git_push_options *opts)
 {
+	git_remote_connect_options connect_opts = GIT_REMOTE_CONNECT_OPTIONS_INIT;
 	int error;
-	const git_remote_callbacks *cbs = NULL;
-	const git_strarray *custom_headers = NULL;
-	const git_proxy_options *proxy = NULL;
 
 	GIT_ASSERT_ARG(remote);
 
@@ -2701,23 +2856,17 @@ int git_remote_push(git_remote *remote, const git_strarray *refspecs, const git_
 		return -1;
 	}
 
-	if (opts) {
-		GIT_ERROR_CHECK_VERSION(&opts->callbacks, GIT_REMOTE_CALLBACKS_VERSION, "git_remote_callbacks");
-		cbs = &opts->callbacks;
-		custom_headers = &opts->custom_headers;
-		GIT_ERROR_CHECK_VERSION(&opts->proxy_opts, GIT_PROXY_OPTIONS_VERSION, "git_proxy_options");
-		proxy = &opts->proxy_opts;
-	}
-
-	if ((error = git_remote_connect(remote, GIT_DIRECTION_PUSH, cbs, proxy, custom_headers)) < 0)
-		return error;
+	if (connect_opts_from_push_opts(&connect_opts, opts) < 0)
+		return -1;
 
 	if ((error = git_remote_upload(remote, refspecs, opts)) < 0)
-		return error;
+		goto done;
 
-	error = git_remote_update_tips(remote, cbs, 0, 0, NULL);
+	error = git_remote_update_tips(remote, &connect_opts.callbacks, 0, 0, NULL);
 
+done:
 	git_remote_disconnect(remote);
+	git_remote_connect_options_dispose(&connect_opts);
 	return error;
 }
 
diff --git a/src/remote.h b/src/remote.h
index 77eefdf..1655e15 100644
--- a/src/remote.h
+++ b/src/remote.h
@@ -37,15 +37,6 @@ struct git_remote {
 	int passed_refspecs;
 };
 
-typedef struct git_remote_connection_opts {
-	const git_strarray *custom_headers;
-	const git_proxy_options *proxy;
-} git_remote_connection_opts;
-
-#define GIT_REMOTE_CONNECTION_OPTIONS_INIT { NULL, NULL }
-
-int git_remote__connect(git_remote *remote, git_direction direction, const git_remote_callbacks *callbacks, const git_remote_connection_opts *conn);
-
 int git_remote__urlfordirection(git_str *url_out, struct git_remote *remote, int direction, const git_remote_callbacks *callbacks);
 int git_remote__http_proxy(char **out, git_remote *remote, git_net_url *url);
 
@@ -54,4 +45,12 @@ git_refspec *git_remote__matching_dst_refspec(git_remote *remote, const char *re
 
 int git_remote__default_branch(git_str *out, git_remote *remote);
 
+int git_remote_connect_options_dup(
+	git_remote_connect_options *dst,
+	const git_remote_connect_options *src);
+int git_remote_connect_options_normalize(
+	git_remote_connect_options *dst,
+	const git_remote_connect_options *src);
+void git_remote_connect_options_dispose(git_remote_connect_options *opts);
+
 #endif
diff --git a/src/transports/http.c b/src/transports/http.c
index adcb1ac..fa576ff 100644
--- a/src/transports/http.c
+++ b/src/transports/http.c
@@ -174,6 +174,7 @@ GIT_INLINE(int) handle_remote_auth(
 	git_http_response *response)
 {
 	http_subtransport *transport = OWNING_SUBTRANSPORT(stream);
+	git_remote_connect_options *connect_opts = &transport->owner->connect_opts;
 
 	if (response->server_auth_credtypes == 0) {
 		git_error_set(GIT_ERROR_HTTP, "server requires authentication that we do not support");
@@ -187,8 +188,8 @@ GIT_INLINE(int) handle_remote_auth(
 		transport->owner->url,
 		response->server_auth_schemetypes,
 		response->server_auth_credtypes,
-		transport->owner->cred_acquire_cb,
-		transport->owner->cred_acquire_payload);
+		connect_opts->callbacks.credentials,
+		connect_opts->callbacks.payload);
 }
 
 GIT_INLINE(int) handle_proxy_auth(
@@ -196,6 +197,7 @@ GIT_INLINE(int) handle_proxy_auth(
 	git_http_response *response)
 {
 	http_subtransport *transport = OWNING_SUBTRANSPORT(stream);
+	git_remote_connect_options *connect_opts = &transport->owner->connect_opts;
 
 	if (response->proxy_auth_credtypes == 0) {
 		git_error_set(GIT_ERROR_HTTP, "proxy requires authentication that we do not support");
@@ -206,11 +208,11 @@ GIT_INLINE(int) handle_proxy_auth(
 	return handle_auth(
 		&transport->proxy,
 		SERVER_TYPE_PROXY,
-		transport->owner->proxy.url,
+		connect_opts->proxy_opts.url,
 		response->server_auth_schemetypes,
 		response->proxy_auth_credtypes,
-		transport->owner->proxy.credentials,
-		transport->owner->proxy.payload);
+		connect_opts->proxy_opts.credentials,
+		connect_opts->proxy_opts.payload);
 }
 
 
@@ -286,6 +288,7 @@ static int lookup_proxy(
 	bool *out_use,
 	http_subtransport *transport)
 {
+	git_remote_connect_options *connect_opts = &transport->owner->connect_opts;
 	const char *proxy;
 	git_remote *remote;
 	char *config = NULL;
@@ -294,9 +297,9 @@ static int lookup_proxy(
 	*out_use = false;
 	git_net_url_dispose(&transport->proxy.url);
 
-	switch (transport->owner->proxy.type) {
+	switch (connect_opts->proxy_opts.type) {
 	case GIT_PROXY_SPECIFIED:
-		proxy = transport->owner->proxy.url;
+		proxy = connect_opts->proxy_opts.url;
 		break;
 
 	case GIT_PROXY_AUTO:
@@ -345,7 +348,7 @@ static int generate_request(
 	request->credentials = transport->server.cred;
 	request->proxy = use_proxy ? &transport->proxy.url : NULL;
 	request->proxy_credentials = transport->proxy.cred;
-	request->custom_headers = &transport->owner->custom_headers;
+	request->custom_headers = &transport->owner->connect_opts.custom_headers;
 
 	if (stream->service->method == GIT_HTTP_METHOD_POST) {
 		request->chunked = stream->service->chunked;
@@ -633,6 +636,7 @@ static int http_action(
 	git_smart_service_t action)
 {
 	http_subtransport *transport = GIT_CONTAINER_OF(t, http_subtransport, parent);
+	git_remote_connect_options *connect_opts = &transport->owner->connect_opts;
 	http_stream *stream;
 	const http_service *service;
 	int error;
@@ -664,10 +668,10 @@ static int http_action(
 	if (!transport->http_client) {
 		git_http_client_options opts = {0};
 
-		opts.server_certificate_check_cb = transport->owner->certificate_check_cb;
-		opts.server_certificate_check_payload = transport->owner->message_cb_payload;
-		opts.proxy_certificate_check_cb = transport->owner->proxy.certificate_check;
-		opts.proxy_certificate_check_payload = transport->owner->proxy.payload;
+		opts.server_certificate_check_cb = connect_opts->callbacks.certificate_check;
+		opts.server_certificate_check_payload = connect_opts->callbacks.payload;
+		opts.proxy_certificate_check_cb = connect_opts->proxy_opts.certificate_check;
+		opts.proxy_certificate_check_payload = connect_opts->proxy_opts.payload;
 
 		if (git_http_client_new(&transport->http_client, &opts) < 0)
 			return -1;
diff --git a/src/transports/local.c b/src/transports/local.c
index 0983914..6065d40 100644
--- a/src/transports/local.c
+++ b/src/transports/local.c
@@ -34,12 +34,9 @@ typedef struct {
 	git_remote *owner;
 	char *url;
 	int direction;
-	int flags;
 	git_atomic32 cancelled;
 	git_repository *repo;
-	git_transport_message_cb progress_cb;
-	git_transport_message_cb error_cb;
-	void *message_cb_payload;
+	git_remote_connect_options connect_opts;
 	git_vector refs;
 	unsigned connected : 1,
 		have_refs : 1;
@@ -200,30 +197,26 @@ on_error:
 static int local_connect(
 	git_transport *transport,
 	const char *url,
-	git_credential_acquire_cb cred_acquire_cb,
-	void *cred_acquire_payload,
-	const git_proxy_options *proxy,
-	int direction, int flags)
+	int direction,
+	const git_remote_connect_options *connect_opts)
 {
 	git_repository *repo;
 	int error;
-	transport_local *t = (transport_local *) transport;
+	transport_local *t = (transport_local *)transport;
 	const char *path;
 	git_str buf = GIT_STR_INIT;
 
-	GIT_UNUSED(cred_acquire_cb);
-	GIT_UNUSED(cred_acquire_payload);
-	GIT_UNUSED(proxy);
-
 	if (t->connected)
 		return 0;
 
+	if (git_remote_connect_options_normalize(&t->connect_opts, connect_opts) < 0)
+		return -1;
+
 	free_heads(&t->refs);
 
 	t->url = git__strdup(url);
 	GIT_ERROR_CHECK_ALLOC(t->url);
 	t->direction = direction;
-	t->flags = flags;
 
 	/* 'url' may be a url or path; convert to a path */
 	if ((error = git_fs_path_from_url_or_path(&buf, url)) < 0) {
@@ -249,6 +242,20 @@ static int local_connect(
 	return 0;
 }
 
+static int local_set_connect_opts(
+	git_transport *transport,
+	const git_remote_connect_options *connect_opts)
+{
+	transport_local *t = (transport_local *)transport;
+
+	if (!t->connected) {
+		git_error_set(GIT_ERROR_NET, "cannot reconfigure a transport that is not connected");
+		return -1;
+	}
+
+	return git_remote_connect_options_normalize(&t->connect_opts, connect_opts);
+}
+
 static int local_ls(const git_remote_head ***out, size_t *size, git_transport *transport)
 {
 	transport_local *t = (transport_local *)transport;
@@ -337,10 +344,10 @@ static int transfer_to_push_transfer(const git_indexer_progress *stats, void *pa
 
 static int local_push(
 	git_transport *transport,
-	git_push *push,
-	const git_remote_callbacks *cbs)
+	git_push *push)
 {
 	transport_local *t = (transport_local *)transport;
+	git_remote_callbacks *cbs = &t->connect_opts.callbacks;
 	git_repository *remote_repo = NULL;
 	push_spec *spec;
 	char *url = NULL;
@@ -349,8 +356,6 @@ static int local_push(
 	int error;
 	size_t j;
 
-	GIT_UNUSED(cbs);
-
 	/* 'push->remote->url' may be a url or path; convert to a path */
 	if ((error = git_fs_path_from_url_or_path(&buf, push->remote->url)) < 0) {
 		git_str_dispose(&buf);
@@ -440,12 +445,11 @@ static int local_push(
 	}
 
 	if (push->specs.length) {
-		int flags = t->flags;
 		url = git__strdup(t->url);
 
 		if (!url || t->parent.close(&t->parent) < 0 ||
 			t->parent.connect(&t->parent, url,
-			NULL, NULL, NULL, GIT_DIRECTION_PUSH, flags))
+			GIT_DIRECTION_PUSH, NULL))
 			goto on_error;
 	}
 
@@ -482,7 +486,7 @@ static int local_counting(int stage, unsigned int current, unsigned int total, v
 	transport_local *t = payload;
 	int error;
 
-	if (!t->progress_cb)
+	if (!t->connect_opts.callbacks.sideband_progress)
 		return 0;
 
 	if (stage == GIT_PACKBUILDER_ADDING_OBJECTS) {
@@ -500,9 +504,19 @@ static int local_counting(int stage, unsigned int current, unsigned int total, v
 	if (git_str_oom(&progress_info))
 		return -1;
 
-	error = t->progress_cb(git_str_cstr(&progress_info), (int)git_str_len(&progress_info), t->message_cb_payload);
-	git_str_dispose(&progress_info);
+	if (progress_info.size > INT_MAX) {
+		git_error_set(GIT_ERROR_NET, "remote sent overly large progress data");
+		git_str_dispose(&progress_info);
+		return -1;
+	}
+
+
+	error = t->connect_opts.callbacks.sideband_progress(
+		progress_info.ptr,
+		(int)progress_info.size,
+		t->connect_opts.callbacks.payload);
 
+	git_str_dispose(&progress_info);
 	return error;
 }
 
@@ -532,9 +546,7 @@ static int foreach_reference_cb(git_reference *reference, void *payload)
 static int local_download_pack(
 		git_transport *transport,
 		git_repository *repo,
-		git_indexer_progress *stats,
-		git_indexer_progress_cb progress_cb,
-		void *progress_payload)
+		git_indexer_progress *stats)
 {
 	transport_local *t = (transport_local*)transport;
 	git_revwalk *walk = NULL;
@@ -545,9 +557,11 @@ static int local_download_pack(
 	git_odb_writepack *writepack = NULL;
 	git_odb *odb = NULL;
 	git_str progress_info = GIT_STR_INIT;
+	foreach_data data = {0};
 
 	if ((error = git_revwalk_new(&walk, t->repo)) < 0)
 		goto cleanup;
+
 	git_revwalk_sorting(walk, GIT_SORT_TIME);
 
 	if ((error = git_packbuilder_new(&pack, t->repo)) < 0)
@@ -583,44 +597,56 @@ static int local_download_pack(
 	if ((error = git_packbuilder_insert_walk(pack, walk)))
 		goto cleanup;
 
-	if ((error = git_str_printf(&progress_info, counting_objects_fmt, git_packbuilder_object_count(pack))) < 0)
-		goto cleanup;
-
-	if (t->progress_cb &&
-	    (error = t->progress_cb(git_str_cstr(&progress_info), (int)git_str_len(&progress_info), t->message_cb_payload)) < 0)
-		goto cleanup;
+	if (t->connect_opts.callbacks.sideband_progress) {
+		if ((error = git_str_printf(
+				&progress_info,
+				counting_objects_fmt,
+				git_packbuilder_object_count(pack))) < 0 ||
+		    (error = t->connect_opts.callbacks.sideband_progress(
+				progress_info.ptr,
+				(int)progress_info.size,
+				t->connect_opts.callbacks.payload)) < 0)
+			goto cleanup;
+	}
 
 	/* Walk the objects, building a packfile */
 	if ((error = git_repository_odb__weakptr(&odb, repo)) < 0)
 		goto cleanup;
 
 	/* One last one with the newline */
-	git_str_clear(&progress_info);
-	git_str_printf(&progress_info, counting_objects_fmt, git_packbuilder_object_count(pack));
-	if ((error = git_str_putc(&progress_info, '\n')) < 0)
-		goto cleanup;
-
-	if (t->progress_cb &&
-	    (error = t->progress_cb(git_str_cstr(&progress_info), (int)git_str_len(&progress_info), t->message_cb_payload)) < 0)
-		goto cleanup;
+	if (t->connect_opts.callbacks.sideband_progress) {
+		git_str_clear(&progress_info);
+
+		if ((error = git_str_printf(
+				&progress_info,
+				counting_objects_fmt,
+				git_packbuilder_object_count(pack))) < 0 ||
+		    (error = git_str_putc(&progress_info, '\n')) < 0 ||
+		    (error = t->connect_opts.callbacks.sideband_progress(
+				progress_info.ptr,
+				(int)progress_info.size,
+				t->connect_opts.callbacks.payload)) < 0)
+			goto cleanup;
+	}
 
-	if ((error = git_odb_write_pack(&writepack, odb, progress_cb, progress_payload)) != 0)
+	if ((error = git_odb_write_pack(
+			&writepack,
+			odb,
+			t->connect_opts.callbacks.transfer_progress,
+			t->connect_opts.callbacks.payload)) < 0)
 		goto cleanup;
 
 	/* Write the data to the ODB */
-	{
-		foreach_data data = {0};
-		data.stats = stats;
-		data.progress_cb = progress_cb;
-		data.progress_payload = progress_payload;
-		data.writepack = writepack;
+	data.stats = stats;
+	data.progress_cb = t->connect_opts.callbacks.transfer_progress;
+	data.progress_payload = t->connect_opts.callbacks.payload;
+	data.writepack = writepack;
 
-		/* autodetect */
-		git_packbuilder_set_threads(pack, 0);
+	/* autodetect */
+	git_packbuilder_set_threads(pack, 0);
 
-		if ((error = git_packbuilder_foreach(pack, foreach_cb, &data)) != 0)
-			goto cleanup;
-	}
+	if ((error = git_packbuilder_foreach(pack, foreach_cb, &data)) != 0)
+		goto cleanup;
 
 	error = writepack->commit(writepack, stats);
 
@@ -632,24 +658,6 @@ cleanup:
 	return error;
 }
 
-static int local_set_callbacks(
-	git_transport *transport,
-	git_transport_message_cb progress_cb,
-	git_transport_message_cb error_cb,
-	git_transport_certificate_check_cb certificate_check_cb,
-	void *message_cb_payload)
-{
-	transport_local *t = (transport_local *)transport;
-
-	GIT_UNUSED(certificate_check_cb);
-
-	t->progress_cb = progress_cb;
-	t->error_cb = error_cb;
-	t->message_cb_payload = message_cb_payload;
-
-	return 0;
-}
-
 static int local_is_connected(git_transport *transport)
 {
 	transport_local *t = (transport_local *)transport;
@@ -657,15 +665,6 @@ static int local_is_connected(git_transport *transport)
 	return t->connected;
 }
 
-static int local_read_flags(git_transport *transport, int *flags)
-{
-	transport_local *t = (transport_local *)transport;
-
-	*flags = t->flags;
-
-	return 0;
-}
-
 static void local_cancel(git_transport *transport)
 {
 	transport_local *t = (transport_local *)transport;
@@ -720,8 +719,8 @@ int git_transport_local(git_transport **out, git_remote *owner, void *param)
 	GIT_ERROR_CHECK_ALLOC(t);
 
 	t->parent.version = GIT_TRANSPORT_VERSION;
-	t->parent.set_callbacks = local_set_callbacks;
 	t->parent.connect = local_connect;
+	t->parent.set_connect_opts = local_set_connect_opts;
 	t->parent.negotiate_fetch = local_negotiate_fetch;
 	t->parent.download_pack = local_download_pack;
 	t->parent.push = local_push;
@@ -729,7 +728,6 @@ int git_transport_local(git_transport **out, git_remote *owner, void *param)
 	t->parent.free = local_free;
 	t->parent.ls = local_ls;
 	t->parent.is_connected = local_is_connected;
-	t->parent.read_flags = local_read_flags;
 	t->parent.cancel = local_cancel;
 
 	if ((error = git_vector_init(&t->refs, 0, NULL)) < 0) {
diff --git a/src/transports/smart.c b/src/transports/smart.c
index fe024de..4267e88 100644
--- a/src/transports/smart.c
+++ b/src/transports/smart.c
@@ -56,101 +56,6 @@ GIT_INLINE(int) git_smart__reset_stream(transport_smart *t, bool close_subtransp
 	return 0;
 }
 
-static int git_smart__set_callbacks(
-	git_transport *transport,
-	git_transport_message_cb progress_cb,
-	git_transport_message_cb error_cb,
-	git_transport_certificate_check_cb certificate_check_cb,
-	void *message_cb_payload)
-{
-	transport_smart *t = GIT_CONTAINER_OF(transport, transport_smart, parent);
-
-	t->progress_cb = progress_cb;
-	t->error_cb = error_cb;
-	t->certificate_check_cb = certificate_check_cb;
-	t->message_cb_payload = message_cb_payload;
-
-	return 0;
-}
-
-static size_t http_header_name_length(const char *http_header)
-{
-	const char *colon = strchr(http_header, ':');
-	if (!colon)
-		return 0;
-	return colon - http_header;
-}
-
-static bool is_malformed_http_header(const char *http_header)
-{
-	const char *c;
-	size_t name_len;
-
-	/* Disallow \r and \n */
-	c = strchr(http_header, '\r');
-	if (c)
-		return true;
-	c = strchr(http_header, '\n');
-	if (c)
-		return true;
-
-	/* Require a header name followed by : */
-	name_len = http_header_name_length(http_header);
-	if (name_len < 1)
-		return true;
-
-	return false;
-}
-
-static char *forbidden_custom_headers[] = {
-	"User-Agent",
-	"Host",
-	"Accept",
-	"Content-Type",
-	"Transfer-Encoding",
-	"Content-Length",
-};
-
-static bool is_forbidden_custom_header(const char *custom_header)
-{
-	unsigned long i;
-	size_t name_len = http_header_name_length(custom_header);
-
-	/* Disallow headers that we set */
-	for (i = 0; i < ARRAY_SIZE(forbidden_custom_headers); i++)
-		if (strncmp(forbidden_custom_headers[i], custom_header, name_len) == 0)
-			return true;
-
-	return false;
-}
-
-static int git_smart__set_custom_headers(
-	git_transport *transport,
-	const git_strarray *custom_headers)
-{
-	transport_smart *t = GIT_CONTAINER_OF(transport, transport_smart, parent);
-	size_t i;
-
-	if (t->custom_headers.count)
-		git_strarray_dispose(&t->custom_headers);
-
-	if (!custom_headers)
-		return 0;
-
-	for (i = 0; i < custom_headers->count; i++) {
-		if (is_malformed_http_header(custom_headers->strings[i])) {
-			git_error_set(GIT_ERROR_INVALID, "custom HTTP header '%s' is malformed", custom_headers->strings[i]);
-			return -1;
-		}
-		if (is_forbidden_custom_header(custom_headers->strings[i])) {
-			git_error_set(GIT_ERROR_INVALID, "custom HTTP header '%s' is already set by libgit2", custom_headers->strings[i]);
-			return -1;
-		}
-	}
-
-	return git_strarray_copy(&t->custom_headers, custom_headers);
-}
-
 int git_smart__update_heads(transport_smart *t, git_vector *symrefs)
 {
 	size_t i;
@@ -206,11 +111,8 @@ static void free_symrefs(git_vector *symrefs)
 static int git_smart__connect(
 	git_transport *transport,
 	const char *url,
-	git_credential_acquire_cb cred_acquire_cb,
-	void *cred_acquire_payload,
-	const git_proxy_options *proxy,
 	int direction,
-	int flags)
+	const git_remote_connect_options *connect_opts)
 {
 	transport_smart *t = GIT_CONTAINER_OF(transport, transport_smart, parent);
 	git_smart_subtransport_stream *stream;
@@ -223,24 +125,19 @@ static int git_smart__connect(
 	if (git_smart__reset_stream(t, true) < 0)
 		return -1;
 
+	if (git_remote_connect_options_normalize(&t->connect_opts, connect_opts) < 0)
+		return -1;
+
 	t->url = git__strdup(url);
 	GIT_ERROR_CHECK_ALLOC(t->url);
 
-	git_proxy_options_clear(&t->proxy);
-
-	if (git_proxy_options_dup(&t->proxy, proxy) < 0)
-		return -1;
-
 	t->direction = direction;
-	t->flags = flags;
-	t->cred_acquire_cb = cred_acquire_cb;
-	t->cred_acquire_payload = cred_acquire_payload;
 
-	if (GIT_DIRECTION_FETCH == t->direction)
+	if (GIT_DIRECTION_FETCH == t->direction) {
 		service = GIT_SERVICE_UPLOADPACK_LS;
-	else if (GIT_DIRECTION_PUSH == t->direction)
+	} else if (GIT_DIRECTION_PUSH == t->direction) {
 		service = GIT_SERVICE_RECEIVEPACK_LS;
-	else {
+	} else {
 		git_error_set(GIT_ERROR_NET, "invalid direction");
 		return -1;
 	}
@@ -315,6 +212,20 @@ cleanup:
 	return error;
 }
 
+static int git_smart__set_connect_opts(
+	git_transport *transport,
+	const git_remote_connect_options *opts)
+{
+	transport_smart *t = GIT_CONTAINER_OF(transport, transport_smart, parent);
+
+	if (!t->connected) {
+		git_error_set(GIT_ERROR_NET, "cannot reconfigure a transport that is not connected");
+		return -1;
+	}
+
+	return git_remote_connect_options_normalize(&t->connect_opts, opts);
+}
+
 static int git_smart__ls(const git_remote_head ***out, size_t *size, git_transport *transport)
 {
 	transport_smart *t = GIT_CONTAINER_OF(transport, transport_smart, parent);
@@ -401,15 +312,6 @@ static int git_smart__is_connected(git_transport *transport)
 	return t->connected;
 }
 
-static int git_smart__read_flags(git_transport *transport, int *flags)
-{
-	transport_smart *t = GIT_CONTAINER_OF(transport, transport_smart, parent);
-
-	*flags = t->flags;
-
-	return 0;
-}
-
 static int git_smart__close(git_transport *transport)
 {
 	transport_smart *t = GIT_CONTAINER_OF(transport, transport_smart, parent);
@@ -465,9 +367,8 @@ static void git_smart__free(git_transport *transport)
 		git_pkt_free(p);
 
 	git_vector_free(refs);
-	git__free((char *)t->proxy.url);
 
-	git_strarray_dispose(&t->custom_headers);
+	git_remote_connect_options_dispose(&t->connect_opts);
 
 	git__free(t);
 }
@@ -482,34 +383,30 @@ static int ref_name_cmp(const void *a, const void *b)
 int git_transport_smart_certificate_check(git_transport *transport, git_cert *cert, int valid, const char *hostname)
 {
 	transport_smart *t = GIT_CONTAINER_OF(transport, transport_smart, parent);
+	git_remote_connect_options *connect_opts = &t->connect_opts;
 
 	GIT_ASSERT_ARG(transport);
 	GIT_ASSERT_ARG(cert);
 	GIT_ASSERT_ARG(hostname);
 
-	if (!t->certificate_check_cb)
+	if (!connect_opts->callbacks.certificate_check)
 		return GIT_PASSTHROUGH;
 
-	return t->certificate_check_cb(cert, valid, hostname, t->message_cb_payload);
+	return connect_opts->callbacks.certificate_check(cert, valid, hostname, connect_opts->callbacks.payload);
 }
 
 int git_transport_smart_credentials(git_credential **out, git_transport *transport, const char *user, int methods)
 {
 	transport_smart *t = GIT_CONTAINER_OF(transport, transport_smart, parent);
+	git_remote_connect_options *connect_opts = &t->connect_opts;
 
 	GIT_ASSERT_ARG(out);
 	GIT_ASSERT_ARG(transport);
 
-	if (!t->cred_acquire_cb)
+	if (!connect_opts->callbacks.credentials)
 		return GIT_PASSTHROUGH;
 
-	return t->cred_acquire_cb(out, t->url, user, methods, t->cred_acquire_payload);
-}
-
-int git_transport_smart_proxy_options(git_proxy_options *out, git_transport *transport)
-{
-	transport_smart *t = GIT_CONTAINER_OF(transport, transport_smart, parent);
-	return git_proxy_options_dup(out, &t->proxy);
+	return connect_opts->callbacks.credentials(out, t->url, user, methods, connect_opts->callbacks.payload);
 }
 
 int git_transport_smart(git_transport **out, git_remote *owner, void *param)
@@ -524,9 +421,8 @@ int git_transport_smart(git_transport **out, git_remote *owner, void *param)
 	GIT_ERROR_CHECK_ALLOC(t);
 
 	t->parent.version = GIT_TRANSPORT_VERSION;
-	t->parent.set_callbacks = git_smart__set_callbacks;
-	t->parent.set_custom_headers = git_smart__set_custom_headers;
 	t->parent.connect = git_smart__connect;
+	t->parent.set_connect_opts = git_smart__set_connect_opts;
 	t->parent.close = git_smart__close;
 	t->parent.free = git_smart__free;
 	t->parent.negotiate_fetch = git_smart__negotiate_fetch;
@@ -534,7 +430,6 @@ int git_transport_smart(git_transport **out, git_remote *owner, void *param)
 	t->parent.push = git_smart__push;
 	t->parent.ls = git_smart__ls;
 	t->parent.is_connected = git_smart__is_connected;
-	t->parent.read_flags = git_smart__read_flags;
 	t->parent.cancel = git_smart__cancel;
 
 	t->owner = owner;
diff --git a/src/transports/smart.h b/src/transports/smart.h
index a9cab31..726bf40 100644
--- a/src/transports/smart.h
+++ b/src/transports/smart.h
@@ -137,16 +137,8 @@ typedef struct {
 	git_transport parent;
 	git_remote *owner;
 	char *url;
-	git_credential_acquire_cb cred_acquire_cb;
-	void *cred_acquire_payload;
-	git_proxy_options proxy;
+	git_remote_connect_options connect_opts;
 	int direction;
-	int flags;
-	git_transport_message_cb progress_cb;
-	git_transport_message_cb error_cb;
-	git_transport_certificate_check_cb certificate_check_cb;
-	void *message_cb_payload;
-	git_strarray custom_headers;
 	git_smart_subtransport *wrapped;
 	git_smart_subtransport_stream *current_stream;
 	transport_smart_caps caps;
@@ -157,8 +149,8 @@ typedef struct {
 	packetsize_cb packetsize_cb;
 	void *packetsize_payload;
 	unsigned rpc : 1,
-		have_refs : 1,
-		connected : 1;
+	         have_refs : 1,
+	         connected : 1;
 	gitno_buffer buffer;
 	char buffer_data[65536];
 } transport_smart;
@@ -166,7 +158,7 @@ typedef struct {
 /* smart_protocol.c */
 int git_smart__store_refs(transport_smart *t, int flushes);
 int git_smart__detect_caps(git_pkt_ref *pkt, transport_smart_caps *caps, git_vector *symrefs);
-int git_smart__push(git_transport *transport, git_push *push, const git_remote_callbacks *cbs);
+int git_smart__push(git_transport *transport, git_push *push);
 
 int git_smart__negotiate_fetch(
 	git_transport *transport,
@@ -177,9 +169,7 @@ int git_smart__negotiate_fetch(
 int git_smart__download_pack(
 	git_transport *transport,
 	git_repository *repo,
-	git_indexer_progress *stats,
-	git_indexer_progress_cb progress_cb,
-	void *progress_payload);
+	git_indexer_progress *stats);
 
 /* smart.c */
 int git_smart__negotiation_step(git_transport *transport, void *data, size_t len);
diff --git a/src/transports/smart_protocol.c b/src/transports/smart_protocol.c
index a9a623c..f1f1117 100644
--- a/src/transports/smart_protocol.c
+++ b/src/transports/smart_protocol.c
@@ -512,9 +512,7 @@ static int network_packetsize(size_t received, void *payload)
 int git_smart__download_pack(
 	git_transport *transport,
 	git_repository *repo,
-	git_indexer_progress *stats,
-	git_indexer_progress_cb progress_cb,
-	void *progress_payload)
+	git_indexer_progress *stats)
 {
 	transport_smart *t = (transport_smart *)transport;
 	gitno_buffer *buf = &t->buffer;
@@ -523,6 +521,10 @@ int git_smart__download_pack(
 	int error = 0;
 	struct network_packetsize_payload npp = {0};
 
+	// TODO
+	git_indexer_progress_cb progress_cb = t->connect_opts.callbacks.transfer_progress;
+	void *progress_payload = t->connect_opts.callbacks.payload;
+
 	memset(stats, 0, sizeof(git_indexer_progress));
 
 	if (progress_cb) {
@@ -568,7 +570,7 @@ int git_smart__download_pack(
 				git_error_clear();
 				error = GIT_EUSER;
 			} else if (pkt->type == GIT_PKT_PROGRESS) {
-				if (t->progress_cb) {
+				if (t->connect_opts.callbacks.sideband_progress) {
 					git_pkt_progress *p = (git_pkt_progress *) pkt;
 
 					if (p->len > INT_MAX) {
@@ -577,7 +579,7 @@ int git_smart__download_pack(
 						goto done;
 					}
 
-					error = t->progress_cb(p->data, (int)p->len, t->message_cb_payload);
+					error = t->connect_opts.callbacks.sideband_progress(p->data, (int)p->len, t->connect_opts.callbacks.payload);
 				}
 			} else if (pkt->type == GIT_PKT_DATA) {
 				git_pkt_data *p = (git_pkt_data *) pkt;
@@ -811,7 +813,7 @@ static int parse_report(transport_smart *transport, git_push *push)
 				error = -1;
 				break;
 			case GIT_PKT_PROGRESS:
-				if (transport->progress_cb) {
+				if (transport->connect_opts.callbacks.sideband_progress) {
 					git_pkt_progress *p = (git_pkt_progress *) pkt;
 
 					if (p->len > INT_MAX) {
@@ -820,7 +822,7 @@ static int parse_report(transport_smart *transport, git_push *push)
 						goto done;
 					}
 
-					error = transport->progress_cb(p->data, (int)p->len, transport->message_cb_payload);
+					error = transport->connect_opts.callbacks.sideband_progress(p->data, (int)p->len, transport->connect_opts.callbacks.payload);
 				}
 				break;
 			default:
@@ -987,9 +989,10 @@ static int stream_thunk(void *buf, size_t size, void *data)
 	return error;
 }
 
-int git_smart__push(git_transport *transport, git_push *push, const git_remote_callbacks *cbs)
+int git_smart__push(git_transport *transport, git_push *push)
 {
 	transport_smart *t = (transport_smart *)transport;
+	git_remote_callbacks *cbs = &t->connect_opts.callbacks;
 	struct push_packbuilder_payload packbuilder_payload = {0};
 	git_str pktline = GIT_STR_INIT;
 	int error = 0, need_pack = 0;
diff --git a/src/transports/ssh.c b/src/transports/ssh.c
index e3bb5ee..f37bf70 100644
--- a/src/transports/ssh.c
+++ b/src/transports/ssh.c
@@ -441,11 +441,15 @@ static int request_creds(git_credential **out, ssh_subtransport *t, const char *
 	int error, no_callback = 0;
 	git_credential *cred = NULL;
 
-	if (!t->owner->cred_acquire_cb) {
+	if (!t->owner->connect_opts.callbacks.credentials) {
 		no_callback = 1;
 	} else {
-		error = t->owner->cred_acquire_cb(&cred, t->owner->url, user, auth_methods,
-						  t->owner->cred_acquire_payload);
+		error = t->owner->connect_opts.callbacks.credentials(
+			&cred,
+			t->owner->url,
+			user,
+			auth_methods,
+			t->owner->connect_opts.callbacks.payload);
 
 		if (error == GIT_PASSTHROUGH) {
 			no_callback = 1;
@@ -558,7 +562,7 @@ post_extract:
 	if ((error = _git_ssh_session_create(&session, s->io)) < 0)
 		goto done;
 
-	if (t->owner->certificate_check_cb != NULL) {
+	if (t->owner->connect_opts.callbacks.certificate_check != NULL) {
 		git_cert_hostkey cert = {{ 0 }}, *cert_ptr;
 		const char *key;
 		size_t cert_len;
@@ -632,7 +636,11 @@ post_extract:
 
 		cert_ptr = &cert;
 
-		error = t->owner->certificate_check_cb((git_cert *) cert_ptr, 0, urldata.host, t->owner->message_cb_payload);
+		error = t->owner->connect_opts.callbacks.certificate_check(
+			(git_cert *)cert_ptr,
+			0,
+			urldata.host,
+			t->owner->connect_opts.callbacks.payload);
 
 		if (error < 0 && error != GIT_PASSTHROUGH) {
 			if (!git_error_last())
diff --git a/src/transports/winhttp.c b/src/transports/winhttp.c
index 60f536f..9b5a67d 100644
--- a/src/transports/winhttp.c
+++ b/src/transports/winhttp.c
@@ -293,14 +293,14 @@ static int certificate_check(winhttp_stream *s, int valid)
 	git_cert_x509 cert;
 
 	/* If there is no override, we should fail if WinHTTP doesn't think it's fine */
-	if (t->owner->certificate_check_cb == NULL && !valid) {
+	if (t->owner->connect_opts.callbacks.certificate_check == NULL && !valid) {
 		if (!git_error_last())
 			git_error_set(GIT_ERROR_HTTP, "unknown certificate check failure");
 
 		return GIT_ECERTIFICATE;
 	}
 
-	if (t->owner->certificate_check_cb == NULL || git__strcmp(t->server.url.scheme, "https") != 0)
+	if (t->owner->connect_opts.callbacks.certificate_check == NULL || git__strcmp(t->server.url.scheme, "https") != 0)
 		return 0;
 
 	if (!WinHttpQueryOption(s->request, WINHTTP_OPTION_SERVER_CERT_CONTEXT, &cert_ctx, &cert_ctx_size)) {
@@ -312,7 +312,7 @@ static int certificate_check(winhttp_stream *s, int valid)
 	cert.parent.cert_type = GIT_CERT_X509;
 	cert.data = cert_ctx->pbCertEncoded;
 	cert.len = cert_ctx->cbCertEncoded;
-	error = t->owner->certificate_check_cb((git_cert *) &cert, valid, t->server.url.host, t->owner->message_cb_payload);
+	error = t->owner->connect_opts.callbacks.certificate_check((git_cert *) &cert, valid, t->server.url.host, t->owner->connect_opts.callbacks.payload);
 	CertFreeCertificateContext(cert_ctx);
 
 	if (error == GIT_PASSTHROUGH)
@@ -426,7 +426,7 @@ static int winhttp_stream_connect(winhttp_stream *s)
 		goto on_error;
 	}
 
-	proxy_opts = &t->owner->proxy;
+	proxy_opts = &t->owner->connect_opts.proxy_opts;
 	if (proxy_opts->type == GIT_PROXY_AUTO) {
 		/* Set proxy if necessary */
 		if (git_remote__http_proxy(&proxy_url, t->owner->owner, &t->server.url) < 0)
@@ -560,10 +560,10 @@ static int winhttp_stream_connect(winhttp_stream *s)
 		}
 	}
 
-	for (i = 0; i < t->owner->custom_headers.count; i++) {
-		if (t->owner->custom_headers.strings[i]) {
+	for (i = 0; i < t->owner->connect_opts.custom_headers.count; i++) {
+		if (t->owner->connect_opts.custom_headers.strings[i]) {
 			git_str_clear(&buf);
-			git_str_puts(&buf, t->owner->custom_headers.strings[i]);
+			git_str_puts(&buf, t->owner->connect_opts.custom_headers.strings[i]);
 			if (git__utf8_to_16(ct, MAX_CONTENT_TYPE_LEN, git_str_cstr(&buf)) < 0) {
 				git_error_set(GIT_ERROR_OS, "failed to convert custom header to wide characters");
 				goto on_error;
@@ -577,14 +577,6 @@ static int winhttp_stream_connect(winhttp_stream *s)
 		}
 	}
 
-	/* If requested, disable certificate validation */
-	if (strcmp(t->server.url.scheme, "https") == 0) {
-		int flags;
-
-		if (t->owner->parent.read_flags(&t->owner->parent, &flags) < 0)
-			goto on_error;
-	}
-
 	if ((error = apply_credentials(s->request, &t->server.url, WINHTTP_AUTH_TARGET_SERVER, t->server.cred, t->server.auth_mechanisms)) < 0)
 		goto on_error;
 
@@ -1218,8 +1210,8 @@ replay:
 			int error = acquire_credentials(s->request,
 				&t->server,
 				t->owner->url,
-				t->owner->cred_acquire_cb,
-				t->owner->cred_acquire_payload);
+				t->owner->connect_opts.callbacks.credentials,
+				t->owner->connect_opts.callbacks.payload);
 
 			if (error < 0) {
 				return error;
@@ -1231,9 +1223,9 @@ replay:
 		} else if (status_code == HTTP_STATUS_PROXY_AUTH_REQ) {
 			int error = acquire_credentials(s->request,
 				&t->proxy,
-				t->owner->proxy.url,
-				t->owner->proxy.credentials,
-				t->owner->proxy.payload);
+				t->owner->connect_opts.proxy_opts.url,
+				t->owner->connect_opts.proxy_opts.credentials,
+				t->owner->connect_opts.proxy_opts.payload);
 
 			if (error < 0) {
 				return error;