diff --git a/Documentation/config.txt b/Documentation/config.txt
index 15c340bd4cafdc..8810839f494e6e 100644
--- a/Documentation/config.txt
+++ b/Documentation/config.txt
@@ -626,6 +626,13 @@ core.fscache::
 Git for Windows uses this to bulk-read and cache lstat data of entire
 directories (instead of doing lstat file by file).
 
+core.longpaths::
+	Enable long path (> 260) support for builtin commands in Git for
+	Windows. This is disabled by default, as long paths are not supported
+	by Windows Explorer, cmd.exe and the Git for Windows tool chain
+	(msys, bash, tcl, perl...). Only enable this if you know what you're
+	doing and are prepared to live with a few quirks.
+
 core.createObject::
 	You can set this to 'link', in which case a hardlink followed by
 	a delete of the source are used to make sure that object creation
diff --git a/cache.h b/cache.h
index c01a84c2a4761a..53f1c29e2da081 100644
--- a/cache.h
+++ b/cache.h
@@ -600,6 +600,8 @@ extern enum hide_dotfiles_type hide_dotfiles;
 
 extern int core_fscache;
 
+extern int core_long_paths;
+
 enum branch_track {
 	BRANCH_TRACK_UNSPECIFIED = -1,
 	BRANCH_TRACK_NEVER = 0,
diff --git a/compat/mingw.c b/compat/mingw.c
index 6627139d3df341..4e44e488579d94 100644
--- a/compat/mingw.c
+++ b/compat/mingw.c
@@ -204,8 +204,8 @@ static int ask_yes_no_if_possible(const char *format, ...)
 int mingw_unlink(const char *pathname)
 {
 	int ret, tries = 0;
-	wchar_t wpathname[MAX_PATH];
-	if (xutftowcs_path(wpathname, pathname) < 0)
+	wchar_t wpathname[MAX_LONG_PATH];
+	if (xutftowcs_long_path(wpathname, pathname) < 0)
 		return -1;
 
 	/* read-only files cannot be removed */
@@ -234,7 +234,7 @@ static int is_dir_empty(const wchar_t *wpath)
 {
 	WIN32_FIND_DATAW findbuf;
 	HANDLE handle;
-	wchar_t wbuf[MAX_PATH + 2];
+	wchar_t wbuf[MAX_LONG_PATH + 2];
 	wcscpy(wbuf, wpath);
 	wcscat(wbuf, L"\\*");
 	handle = FindFirstFileW(wbuf, &findbuf);
@@ -255,8 +255,8 @@ static int is_dir_empty(const wchar_t *wpath)
 int mingw_rmdir(const char *pathname)
 {
 	int ret, tries = 0;
-	wchar_t wpathname[MAX_PATH];
-	if (xutftowcs_path(wpathname, pathname) < 0)
+	wchar_t wpathname[MAX_LONG_PATH];
+	if (xutftowcs_long_path(wpathname, pathname) < 0)
 		return -1;
 
 	while ((ret = _wrmdir(wpathname)) == -1 && tries < ARRAY_SIZE(delay)) {
@@ -296,9 +296,9 @@ static int make_hidden(const wchar_t *path)
 
 void mingw_mark_as_git_dir(const char *dir)
 {
-	wchar_t wdir[MAX_PATH];
+	wchar_t wdir[MAX_LONG_PATH];
 	if (hide_dotfiles != HIDE_DOTFILES_FALSE && !is_bare_repository())
-		if (xutftowcs_path(wdir, dir) < 0 || make_hidden(wdir))
+		if (xutftowcs_long_path(wdir, dir) < 0 || make_hidden(wdir))
 			warning("Failed to make '%s' hidden", dir);
 	git_config_set("core.hideDotFiles",
 		hide_dotfiles == HIDE_DOTFILES_FALSE ? "false" :
@@ -309,9 +309,12 @@ void mingw_mark_as_git_dir(const char *dir)
 int mingw_mkdir(const char *path, int mode)
 {
 	int ret;
-	wchar_t wpath[MAX_PATH];
-	if (xutftowcs_path(wpath, path) < 0)
+	wchar_t wpath[MAX_LONG_PATH];
+	/* CreateDirectoryW path limit is 248 (MAX_PATH - 8.3 file name) */
+	if (xutftowcs_path_ex(wpath, path, MAX_LONG_PATH, -1, 248,
+			core_long_paths) < 0)
 		return -1;
+
 	ret = _wmkdir(wpath);
 	if (!ret && hide_dotfiles == HIDE_DOTFILES_TRUE) {
 		/*
@@ -331,7 +334,7 @@ int mingw_open (const char *filename, int oflags, ...)
 	va_list args;
 	unsigned mode;
 	int fd;
-	wchar_t wfilename[MAX_PATH];
+	wchar_t wfilename[MAX_LONG_PATH];
 
 	va_start(args, oflags);
 	mode = va_arg(args, int);
@@ -340,7 +343,7 @@ int mingw_open (const char *filename, int oflags, ...)
 	if (filename && !strcmp(filename, "/dev/null"))
 		filename = "nul";
 
-	if (xutftowcs_path(wfilename, filename) < 0)
+	if (xutftowcs_long_path(wfilename, filename) < 0)
 		return -1;
 	fd = _wopen(wfilename, oflags, mode);
 
@@ -410,13 +413,13 @@ FILE *mingw_fopen (const char *filename, const char *otype)
 {
 	int hide = 0;
 	FILE *file;
-	wchar_t wfilename[MAX_PATH], wotype[4];
+	wchar_t wfilename[MAX_LONG_PATH], wotype[4];
 	if (hide_dotfiles == HIDE_DOTFILES_TRUE &&
 	    basename((char*)filename)[0] == '.')
 		hide = access(filename, F_OK);
 	if (filename && !strcmp(filename, "/dev/null"))
 		filename = "nul";
-	if (xutftowcs_path(wfilename, filename) < 0 ||
+	if (xutftowcs_long_path(wfilename, filename) < 0 ||
 		xutftowcs(wotype, otype, ARRAY_SIZE(wotype)) < 0)
 		return NULL;
 	file = _wfopen(wfilename, wotype);
@@ -429,13 +432,13 @@ FILE *mingw_freopen (const char *filename, const char *otype, FILE *stream)
 {
 	int hide = 0;
 	FILE *file;
-	wchar_t wfilename[MAX_PATH], wotype[4];
+	wchar_t wfilename[MAX_LONG_PATH], wotype[4];
 	if (hide_dotfiles == HIDE_DOTFILES_TRUE &&
 	    basename((char*)filename)[0] == '.')
 		hide = access(filename, F_OK);
 	if (filename && !strcmp(filename, "/dev/null"))
 		filename = "nul";
-	if (xutftowcs_path(wfilename, filename) < 0 ||
+	if (xutftowcs_long_path(wfilename, filename) < 0 ||
 		xutftowcs(wotype, otype, ARRAY_SIZE(wotype)) < 0)
 		return NULL;
 	file = _wfreopen(wfilename, wotype, stream);
@@ -468,25 +471,32 @@ int mingw_fflush(FILE *stream)
 
 int mingw_access(const char *filename, int mode)
 {
-	wchar_t wfilename[MAX_PATH];
-	if (xutftowcs_path(wfilename, filename) < 0)
+	wchar_t wfilename[MAX_LONG_PATH];
+	if (xutftowcs_long_path(wfilename, filename) < 0)
 		return -1;
 	/* X_OK is not supported by the MSVCRT version */
 	return _waccess(wfilename, mode & ~X_OK);
 }
 
+/* cached length of current directory for handle_long_path */
+static int current_directory_len = 0;
+
 int mingw_chdir(const char *dirname)
 {
+	int result;
 	wchar_t wdirname[MAX_PATH];
+	/* SetCurrentDirectoryW doesn't support long paths */
 	if (xutftowcs_path(wdirname, dirname) < 0)
 		return -1;
-	return _wchdir(wdirname);
+	result = _wchdir(wdirname);
+	current_directory_len = GetCurrentDirectoryW(0, NULL);
+	return result;
 }
 
 int mingw_chmod(const char *filename, int mode)
 {
-	wchar_t wfilename[MAX_PATH];
-	if (xutftowcs_path(wfilename, filename) < 0)
+	wchar_t wfilename[MAX_LONG_PATH];
+	if (xutftowcs_long_path(wfilename, filename) < 0)
 		return -1;
 	return _wchmod(wfilename, mode);
 }
@@ -501,8 +511,8 @@ int mingw_chmod(const char *filename, int mode)
 static int do_lstat(int follow, const char *file_name, struct stat *buf)
 {
 	WIN32_FILE_ATTRIBUTE_DATA fdata;
-	wchar_t wfilename[MAX_PATH];
-	if (xutftowcs_path(wfilename, file_name) < 0)
+	wchar_t wfilename[MAX_LONG_PATH];
+	if (xutftowcs_long_path(wfilename, file_name) < 0)
 		return -1;
 
 	if (GetFileAttributesExW(wfilename, GetFileExInfoStandard, &fdata)) {
@@ -645,8 +655,8 @@ int mingw_utime (const char *file_name, const struct utimbuf *times)
 	FILETIME mft, aft;
 	int fh, rc;
 	DWORD attrs;
-	wchar_t wfilename[MAX_PATH];
-	if (xutftowcs_path(wfilename, file_name) < 0)
+	wchar_t wfilename[MAX_LONG_PATH];
+	if (xutftowcs_long_path(wfilename, file_name) < 0)
 		return -1;
 
 	/* must have write permission */
@@ -694,6 +704,7 @@ unsigned int sleep (unsigned int seconds)
 char *mingw_mktemp(char *template)
 {
 	wchar_t wtemplate[MAX_PATH];
+	/* we need to return the path, thus no long paths here! */
 	if (xutftowcs_path(wtemplate, template) < 0)
 		return NULL;
 	if (!_wmktemp(wtemplate))
@@ -1136,6 +1147,7 @@ static pid_t mingw_spawnve_fd(const char *cmd, const char **argv, char **deltaen
 	si.hStdOutput = winansi_get_osfhandle(fhout);
 	si.hStdError = winansi_get_osfhandle(fherr);
 
+	/* executables and the current directory don't support long paths */
 	if (xutftowcs_path(wcmd, cmd) < 0)
 		return -1;
 	if (dir && xutftowcs_path(wdir, dir) < 0)
@@ -1628,8 +1640,9 @@ int mingw_rename(const char *pold, const char *pnew)
 {
 	DWORD attrs, gle;
 	int tries = 0;
-	wchar_t wpold[MAX_PATH], wpnew[MAX_PATH];
-	if (xutftowcs_path(wpold, pold) < 0 || xutftowcs_path(wpnew, pnew) < 0)
+	wchar_t wpold[MAX_LONG_PATH], wpnew[MAX_LONG_PATH];
+	if (xutftowcs_long_path(wpold, pold) < 0 ||
+	    xutftowcs_long_path(wpnew, pnew) < 0)
 		return -1;
 
 	/*
@@ -1905,9 +1918,9 @@ int link(const char *oldpath, const char *newpath)
 {
 	typedef BOOL (WINAPI *T)(LPCWSTR, LPCWSTR, LPSECURITY_ATTRIBUTES);
 	static T create_hard_link = NULL;
-	wchar_t woldpath[MAX_PATH], wnewpath[MAX_PATH];
-	if (xutftowcs_path(woldpath, oldpath) < 0 ||
-		xutftowcs_path(wnewpath, newpath) < 0)
+	wchar_t woldpath[MAX_LONG_PATH], wnewpath[MAX_LONG_PATH];
+	if (xutftowcs_long_path(woldpath, oldpath) < 0 ||
+	    xutftowcs_long_path(wnewpath, newpath) < 0)
 		return -1;
 
 	if (!create_hard_link) {
@@ -2106,6 +2119,61 @@ int xwcstoutf(char *utf, const wchar_t *wcs, size_t utflen)
 	return -1;
 }
 
+int handle_long_path(wchar_t *path, int len, int max_path, int expand)
+{
+	int result;
+	wchar_t buf[MAX_LONG_PATH];
+
+	/*
+	 * we don't need special handling if path is relative to the current
+	 * directory, and current directory + path don't exceed the desired
+	 * max_path limit. This should cover > 99 % of cases with minimal
+	 * performance impact (git almost always uses relative paths).
+	 */
+	if ((len < 2 || (!is_dir_sep(path[0]) && path[1] != ':')) &&
+	    (current_directory_len + len < max_path))
+		return len;
+
+	/*
+	 * handle everything else:
+	 * - absolute paths: "C:\dir\file"
+	 * - absolute UNC paths: "\\server\share\dir\file"
+	 * - absolute paths on current drive: "\dir\file"
+	 * - relative paths on other drive: "X:file"
+	 * - prefixed paths: "\\?\...", "\\.\..."
+	 */
+
+	/* convert to absolute path using GetFullPathNameW */
+	result = GetFullPathNameW(path, MAX_LONG_PATH, buf, NULL);
+	if (!result) {
+		errno = err_win_to_posix(GetLastError());
+		return -1;
+	}
+	/* keep original path if its full path doesn't exceed max_path */
+	if (result < max_path)
+		return len;
+	/* error out if we shouldn't expand the path or buf is too small */
+	if (!expand || result >= MAX_LONG_PATH - 6) {
+		errno = ENAMETOOLONG;
+		return -1;
+	}
+
+	/* prefix full path with "\\?\" or "\\?\UNC\" */
+	if (buf[0] == '\\') {
+		/* ...unless already prefixed */
+		if (buf[1] == '\\' && (buf[2] == '?' || buf[2] == '.'))
+			return len;
+
+		wcscpy(path, L"\\\\?\\UNC\\");
+		wcscpy(path + 8, buf + 2);
+		return result + 6;
+	} else {
+		wcscpy(path, L"\\\\?\\");
+		wcscpy(path + 4, buf);
+		return result + 4;
+	}
+}
+
 /*
  * Disable MSVCRT command line wildcard expansion (__getmainargs called from
  * mingw startup code, see init.c in mingw runtime).
@@ -2209,4 +2277,7 @@ void mingw_startup()
 
 	/* initialize Unicode console */
 	winansi_init();
+
+	/* init length of current directory for handle_long_path */
+	current_directory_len = GetCurrentDirectoryW(0, NULL);
 }
diff --git a/compat/mingw.h b/compat/mingw.h
index 28f6eef5b11764..b06861ed4c16b0 100644
--- a/compat/mingw.h
+++ b/compat/mingw.h
@@ -379,6 +379,39 @@ void mingw_open_html(const char *path);
 void mingw_mark_as_git_dir(const char *dir);
 #define mark_as_git_dir mingw_mark_as_git_dir
 
+/**
+ * Max length of long paths (exceeding MAX_PATH). The actual maximum supported
+ * by NTFS is 32,767 (* sizeof(wchar_t)), but we choose an arbitrary smaller
+ * value to limit required stack memory.
+ */
+#define MAX_LONG_PATH 4096
+
+/**
+ * Handles paths that would exceed the MAX_PATH limit of Windows Unicode APIs.
+ *
+ * With expand == false, the function only checks for over-long path and fails
+ * with ENAMETOOLONG. The path parameter is not modified.
+ *
+ * With expand == true, an over-long path is automatically converted in place
+ * to an absolute path prefixed with '\\?\', and the new length is returned.
+ * The path parameter must point to a buffer of MAX_LONG_PATH wide characters.
+ *
+ * Parameters:
+ * path: path to check and / or convert
+ * len: size of path on input (number of wide chars without \0)
+ * max_path: max short path length to check (usually MAX_PATH = 260, but just
+ * 248 for CreateDirectoryW)
+ * expand: false to only check the length, true to expand the path to a
+ * '\\?\'-prefixed absolute path
+ *
+ * Return:
+ * length of the resulting path, or -1 on failure
+ *
+ * Errors:
+ * ENAMETOOLONG if path is too long
+ */
+int handle_long_path(wchar_t *path, int len, int max_path, int expand);
+
 /**
  * Converts UTF-8 encoded string to UTF-16LE.
  *
@@ -437,18 +470,49 @@ static inline int xutftowcs(wchar_t *wcs, const char *utf, size_t wcslen)
 }
 
 /**
- * Simplified file system specific variant of xutftowcsn, assumes output
- * buffer size is MAX_PATH wide chars and input string is \0-terminated,
- * fails with ENAMETOOLONG if input string is too long.
+ * Simplified file system specific wrapper of xutftowcsn and handle_long_path.
+ * Converts ERANGE to ENAMETOOLONG. If expand is true, wcs must be at least
+ * MAX_LONG_PATH wide chars (see handle_long_path).
  */
-static inline int xutftowcs_path(wchar_t *wcs, const char *utf)
+static inline int xutftowcs_path_ex(wchar_t *wcs, const char *utf,
+		size_t wcslen, int utflen, int max_path, int expand)
 {
-	int result = xutftowcsn(wcs, utf, MAX_PATH, -1);
+	int result = xutftowcsn(wcs, utf, wcslen, utflen);
 	if (result < 0 && errno == ERANGE)
 		errno = ENAMETOOLONG;
+	if (result >= 0)
+		result = handle_long_path(wcs, result, max_path, expand);
 	return result;
 }
 
+/**
+ * Simplified file system specific variant of xutftowcsn, assumes output
+ * buffer size is MAX_PATH wide chars and input string is \0-terminated,
+ * fails with ENAMETOOLONG if input string is too long. Typically used for
+ * Windows APIs that don't support long paths, e.g. SetCurrentDirectory,
+ * LoadLibrary, CreateProcess...
+ */
+static inline int xutftowcs_path(wchar_t *wcs, const char *utf)
+{
+	return xutftowcs_path_ex(wcs, utf, MAX_PATH, -1, MAX_PATH, 0);
+}
+
+/* need to re-declare that here as mingw.h is included before cache.h */
+extern int core_long_paths;
+
+/**
+ * Simplified file system specific variant of xutftowcsn for Windows APIs
+ * that support long paths via '\\?\'-prefix, assumes output buffer size is
+ * MAX_LONG_PATH wide chars, fails with ENAMETOOLONG if input string is too
+ * long. The 'core.longpaths' git-config option controls whether the path
+ * is only checked or expanded to a long path.
+ */
+static inline int xutftowcs_long_path(wchar_t *wcs, const char *utf)
+{
+	return xutftowcs_path_ex(wcs, utf, MAX_LONG_PATH, -1, MAX_PATH,
+			core_long_paths);
+}
+
 /**
  * Converts UTF-16LE encoded string to UTF-8.
  *
diff --git a/compat/win32/dirent.c b/compat/win32/dirent.c
index 6b87042182d950..c18fd0024cf316 100644
--- a/compat/win32/dirent.c
+++ b/compat/win32/dirent.c
@@ -63,19 +63,22 @@ static int dirent_closedir(dirent_DIR *dir)
 
 DIR *dirent_opendir(const char *name)
 {
-	wchar_t pattern[MAX_PATH + 2]; /* + 2 for '/' '*' */
+	wchar_t pattern[MAX_LONG_PATH + 2]; /* + 2 for "\*" */
 	WIN32_FIND_DATAW fdata;
 	HANDLE h;
 	int len;
 	dirent_DIR *dir;
 
-	/* convert name to UTF-16 and check length < MAX_PATH */
-	if ((len = xutftowcs_path(pattern, name)) < 0)
+	/* convert name to UTF-16 and check length */
+	if ((len = xutftowcs_long_path(pattern, name)) < 0)
 		return NULL;
 
-	/* append optional '/' and wildcard '*' */
+	/*
+	 * append optional '\' and wildcard '*'. Note: we need to use '\' as
+	 * Windows doesn't translate '/' to '\' for "\\?\"-prefixed paths.
+	 */
 	if (len && !is_dir_sep(pattern[len - 1]))
-		pattern[len++] = '/';
+		pattern[len++] = '\\';
 	pattern[len++] = '*';
 	pattern[len] = 0;
 
diff --git a/compat/win32/fscache.c b/compat/win32/fscache.c
index 5388d64377b700..da3bb2cae1d05e 100644
--- a/compat/win32/fscache.c
+++ b/compat/win32/fscache.c
@@ -162,23 +162,24 @@ static struct fsentry *fseentry_create_entry(struct fsentry *list,
  */
 static struct fsentry *fsentry_create_list(const struct fsentry *dir)
 {
-	wchar_t pattern[MAX_PATH + 2]; /* + 2 for '/' '*' */
+	wchar_t pattern[MAX_LONG_PATH + 2]; /* + 2 for "\*" */
 	WIN32_FIND_DATAW fdata;
 	HANDLE h;
 	int wlen;
 	struct fsentry *list, **phead;
 	DWORD err;
 
-	/* convert name to UTF-16 and check length < MAX_PATH */
-	if ((wlen = xutftowcsn(pattern, dir->name, MAX_PATH, dir->len)) < 0) {
-		if (errno == ERANGE)
-			errno = ENAMETOOLONG;
+	/* convert name to UTF-16 and check length */
+	if ((wlen = xutftowcs_path_ex(pattern, dir->name, MAX_LONG_PATH,
+			dir->len, MAX_PATH - 2, core_long_paths)) < 0)
 		return NULL;
-	}
 
-	/* append optional '/' and wildcard '*' */
+	/*
+	 * append optional '\' and wildcard '*'. Note: we need to use '\' as
+	 * Windows doesn't translate '/' to '\' for "\\?\"-prefixed paths.
+	 */
 	if (wlen)
-		pattern[wlen++] = '/';
+		pattern[wlen++] = '\\';
 	pattern[wlen++] = '*';
 	pattern[wlen] = 0;
 
diff --git a/config.c b/config.c
index 2edf1e7b0f93a3..fb6ad8cedce944 100644
--- a/config.c
+++ b/config.c
@@ -895,6 +895,11 @@ static int git_default_core_config(const char *var, const char *value)
 		return 0;
 	}
 
+	if (!strcmp(var, "core.longpaths")) {
+		core_long_paths = git_config_bool(var, value);
+		return 0;
+	}
+
 	/* Add other config variables here and to Documentation/config.txt. */
 	return 0;
 }
diff --git a/environment.c b/environment.c
index 66d67acda37c4a..697093d3185d8a 100644
--- a/environment.c
+++ b/environment.c
@@ -64,6 +64,7 @@ struct startup_info *startup_info;
 unsigned long pack_size_limit_cfg;
 enum hide_dotfiles_type hide_dotfiles = HIDE_DOTFILES_DOTGITONLY;
 int core_fscache;
+int core_long_paths;
 
 /*
  * The character that begins a commented line in user-editable file