diff --git a/compat/mingw.c b/compat/mingw.c
index 15f0b4a45821b9..76d853357edab3 100644
--- a/compat/mingw.c
+++ b/compat/mingw.c
@@ -2625,6 +2625,47 @@ int xwcstoutf(char *utf, const wchar_t *wcs, size_t utflen)
 	return -1;
 }
 
+#ifdef ENSURE_MSYSTEM_IS_SET
+static size_t append_system_bin_dirs(char *path, size_t size)
+{
+#if !defined(RUNTIME_PREFIX) || !defined(HAVE_WPGMPTR)
+	return 0;
+#else
+	char prefix[32768];
+	const char *slash;
+	size_t len = xwcstoutf(prefix, _wpgmptr, sizeof(prefix)), off = 0;
+
+	if (len == 0 || len >= sizeof(prefix) ||
+	    !(slash = find_last_dir_sep(prefix)))
+		return 0;
+	/* strip trailing `git.exe` */
+	len = slash - prefix;
+
+	/* strip trailing `cmd` or `mingw64\bin` or `mingw32\bin` or `bin` or `libexec\git-core` */
+	if (strip_suffix_mem(prefix, &len, "\\mingw64\\libexec\\git-core") ||
+	    strip_suffix_mem(prefix, &len, "\\mingw64\\bin"))
+		off += xsnprintf(path + off, size - off,
+				 "%.*s\\mingw64\\bin;", (int)len, prefix);
+	else if (strip_suffix_mem(prefix, &len, "\\mingw32\\libexec\\git-core") ||
+		 strip_suffix_mem(prefix, &len, "\\mingw32\\bin"))
+		off += xsnprintf(path + off, size - off,
+				 "%.*s\\mingw32\\bin;", (int)len, prefix);
+	else if (strip_suffix_mem(prefix, &len, "\\cmd") ||
+		 strip_suffix_mem(prefix, &len, "\\bin") ||
+		 strip_suffix_mem(prefix, &len, "\\libexec\\git-core"))
+		off += xsnprintf(path + off, size - off,
+				 "%.*s\\mingw%d\\bin;", (int)len, prefix,
+				 (int)(sizeof(void *) * 8));
+	else
+		return 0;
+
+	off += xsnprintf(path + off, size - off,
+			 "%.*s\\usr\\bin;", (int)len, prefix);
+	return off;
+#endif
+}
+#endif
+
 static void setup_windows_environment(void)
 {
 	char *tmp = getenv("TMPDIR");
@@ -2677,6 +2718,34 @@ static void setup_windows_environment(void)
 			setenv("HOME", tmp, 1);
 	}
 
+	if (!getenv("PLINK_PROTOCOL"))
+		setenv("PLINK_PROTOCOL", "ssh", 0);
+
+#ifdef ENSURE_MSYSTEM_IS_SET
+	if (!(tmp = getenv("MSYSTEM")) || !tmp[0]) {
+		const char *home = getenv("HOME"), *path = getenv("PATH");
+		char buf[32768];
+		size_t off = 0;
+
+		xsnprintf(buf, sizeof(buf),
+			  "MINGW%d", (int)(sizeof(void *) * 8));
+		setenv("MSYSTEM", buf, 1);
+
+		if (home)
+			off += xsnprintf(buf + off, sizeof(buf) - off,
+					 "%s\\bin;", home);
+		off += append_system_bin_dirs(buf + off, sizeof(buf) - off);
+		if (path)
+			off += xsnprintf(buf + off, sizeof(buf) - off,
+					 "%s", path);
+		else if (off > 0)
+			buf[off - 1] = '\0';
+		else
+			buf[0] = '\0';
+		setenv("PATH", buf, 1);
+	}
+#endif
+
 	if (!getenv("LC_ALL") && !getenv("LC_CTYPE") && !getenv("LANG"))
 		setenv("LC_CTYPE", "C.UTF-8", 1);
 }
diff --git a/config.mak.uname b/config.mak.uname
index 693dcd47149115..a410e683fc61bd 100644
--- a/config.mak.uname
+++ b/config.mak.uname
@@ -506,7 +506,7 @@ endif
 		compat/win32/pthread.o compat/win32/syslog.o \
 		compat/win32/trace2_win32_process_info.o \
 		compat/win32/dirent.o
-	COMPAT_CFLAGS = -D__USE_MINGW_ACCESS -DDETECT_MSYS_TTY -DNOGDI -DHAVE_STRING_H -Icompat -Icompat/regex -Icompat/win32 -DSTRIP_EXTENSION=\".exe\"
+	COMPAT_CFLAGS = -D__USE_MINGW_ACCESS -DDETECT_MSYS_TTY -DENSURE_MSYSTEM_IS_SET -DNOGDI -DHAVE_STRING_H -Icompat -Icompat/regex -Icompat/win32 -DSTRIP_EXTENSION=\".exe\"
 	BASIC_LDFLAGS = -IGNORE:4217 -IGNORE:4049 -NOLOGO -ENTRY:wmainCRTStartup -SUBSYSTEM:CONSOLE
 	# invalidcontinue.obj allows Git's source code to close the same file
 	# handle twice, or to access the osfhandle of an already-closed stdout
@@ -735,7 +735,7 @@ ifeq ($(uname_S),MINGW)
         endif
 	CC = gcc
 	COMPAT_CFLAGS += -D__USE_MINGW_ANSI_STDIO=0 -DDETECT_MSYS_TTY \
-		-fstack-protector-strong
+		-DENSURE_MSYSTEM_IS_SET -fstack-protector-strong
 	EXTLIBS += -lntdll
 	EXTRA_PROGRAMS += headless-git$X
 	INSTALL = /bin/install
diff --git a/t/t0060-path-utils.sh b/t/t0060-path-utils.sh
index 0afa3d0d312ca6..e73835e41b96e4 100755
--- a/t/t0060-path-utils.sh
+++ b/t/t0060-path-utils.sh
@@ -599,7 +599,8 @@ test_expect_success !VALGRIND,RUNTIME_PREFIX,CAN_EXEC_IN_PWD 'RUNTIME_PREFIX wor
 	cp "$GIT_EXEC_PATH"/git$X pretend/bin/ &&
 	GIT_EXEC_PATH= ./pretend/bin/git here >actual &&
 	echo HERE >expect &&
-	test_cmp expect actual'
+	test_cmp expect actual
+'
 
 test_expect_success !VALGRIND,RUNTIME_PREFIX,CAN_EXEC_IN_PWD '%(prefix)/ works' '
 	mkdir -p pretend/bin &&
@@ -610,4 +611,32 @@ test_expect_success !VALGRIND,RUNTIME_PREFIX,CAN_EXEC_IN_PWD '%(prefix)/ works'
 	test_cmp expect actual
 '
 
+test_expect_success MINGW 'MSYSTEM/PATH is adjusted if necessary' '
+	mkdir -p "$HOME"/bin pretend/mingw64/bin \
+		pretend/mingw64/libexec/git-core pretend/usr/bin &&
+	cp "$GIT_EXEC_PATH"/git.exe pretend/mingw64/bin/ &&
+	cp "$GIT_EXEC_PATH"/git.exe pretend/mingw64/libexec/git-core/ &&
+	# copy the .dll files, if any (happens when building via CMake)
+	case "$GIT_EXEC_PATH"/*.dll in
+	*/"*.dll") ;; # no `.dll` files to be copied
+	*)
+		cp "$GIT_EXEC_PATH"/*.dll pretend/mingw64/bin/ &&
+		cp "$GIT_EXEC_PATH"/*.dll pretend/mingw64/libexec/git-core/
+		;;
+	esac &&
+	echo "env | grep MSYSTEM=" | write_script "$HOME"/bin/git-test-home &&
+	echo "echo mingw64" | write_script pretend/mingw64/bin/git-test-bin &&
+	echo "echo usr" | write_script pretend/usr/bin/git-test-bin2 &&
+
+	(
+		MSYSTEM= &&
+		GIT_EXEC_PATH= &&
+		pretend/mingw64/libexec/git-core/git.exe test-home >actual &&
+		pretend/mingw64/libexec/git-core/git.exe test-bin >>actual &&
+		pretend/mingw64/bin/git.exe test-bin2 >>actual
+	) &&
+	test_write_lines MSYSTEM=$MSYSTEM mingw64 usr >expect &&
+	test_cmp expect actual
+'
+
 test_done