diff --git a/frontend/dockerfile/dockerfile_test.go b/frontend/dockerfile/dockerfile_test.go
index 8d4f25401752..526d00e54cd8 100644
--- a/frontend/dockerfile/dockerfile_test.go
+++ b/frontend/dockerfile/dockerfile_test.go
@@ -152,6 +152,7 @@ var allTests = integration.TestFuncs(
 	testNamedMultiplatformInputContext,
 	testNamedFilteredContext,
 	testEmptyDestDir,
+	testPreserveDestDirSlash,
 	testCopyLinkDotDestDir,
 	testCopyLinkEmptyDestDir,
 	testCopyChownCreateDest,
@@ -547,6 +548,42 @@ RUN cmd /V:on /C "set /p tfcontent=<testfile \
 	require.NoError(t, err)
 }
 
+func testPreserveDestDirSlash(t *testing.T, sb integration.Sandbox) {
+	f := getFrontend(t, sb)
+
+	dockerfile := []byte(integration.UnixOrWindows(
+		`
+FROM busybox
+COPY testfile /sample/
+RUN [ "$(cat /sample/testfile)" == "contents0" ]
+`,
+		`
+FROM nanoserver
+COPY testfile /sample/
+RUN cmd /V:on /C "set /p tfcontent=<\sample\testfile \
+	& if !tfcontent! NEQ contents0 (exit 1)"
+`,
+	))
+
+	dir := integration.Tmpdir(
+		t,
+		fstest.CreateFile("Dockerfile", dockerfile, 0600),
+		fstest.CreateFile("testfile", []byte("contents0"), 0600),
+	)
+
+	c, err := client.New(sb.Context(), sb.Address())
+	require.NoError(t, err)
+	defer c.Close()
+
+	_, err = f.Solve(sb.Context(), c, client.SolveOpt{
+		LocalMounts: map[string]fsutil.FS{
+			dockerui.DefaultLocalNameDockerfile: dir,
+			dockerui.DefaultLocalNameContext:    dir,
+		},
+	}, nil)
+	require.NoError(t, err)
+}
+
 func testCopyLinkDotDestDir(t *testing.T, sb integration.Sandbox) {
 	integration.SkipOnPlatform(t, "windows")
 	f := getFrontend(t, sb)
diff --git a/util/system/path.go b/util/system/path.go
index cdfff68007f5..b2bf10e57dc2 100644
--- a/util/system/path.go
+++ b/util/system/path.go
@@ -193,9 +193,11 @@ func CheckSystemDriveAndRemoveDriveLetter(path string, inputOS string) (string,
 	}
 
 	parts := strings.SplitN(path, ":", 2)
+
 	// Path does not have a drive letter. Just return it.
 	if len(parts) < 2 {
-		return ToSlash(filepath.Clean(path), inputOS), nil
+		cleanedPath := filepath.Clean(path)
+		return ToSlash(keepTrailingSlash(cleanedPath, path, inputOS), inputOS), nil
 	}
 
 	// We expect all paths to be in C:
@@ -220,5 +222,6 @@ func CheckSystemDriveAndRemoveDriveLetter(path string, inputOS string) (string,
 	//
 	// We must return the second element of the split path, as is, without attempting to convert
 	// it to an absolute path. We have no knowledge of the CWD; that is treated elsewhere.
-	return ToSlash(filepath.Clean(parts[1]), inputOS), nil
+	cleanedPath := filepath.Clean(parts[1])
+	return ToSlash(keepTrailingSlash(cleanedPath, parts[1], inputOS), inputOS), nil
 }
diff --git a/util/system/path_unix.go b/util/system/path_unix.go
new file mode 100644
index 000000000000..33e51956187e
--- /dev/null
+++ b/util/system/path_unix.go
@@ -0,0 +1,10 @@
+//go:build !windows
+// +build !windows
+
+package system
+
+// this was addressing a Windows-specific issue #5249,
+// does nothing on unix.
+func keepTrailingSlash(cleanedPath, _, _ string) string {
+	return cleanedPath
+}
diff --git a/util/system/path_windows.go b/util/system/path_windows.go
new file mode 100644
index 000000000000..d437998220ee
--- /dev/null
+++ b/util/system/path_windows.go
@@ -0,0 +1,17 @@
+package system
+
+import "strings"
+
+// Checks if a path other than root has a trailing slash
+// and retains it. See https://github.com/moby/buildkit/issues/5249
+// Expects cleanedPath to have gone through filepath.Clean
+func keepTrailingSlash(cleanedPath, origPath, inputOS string) string {
+	hasTrailingSlash := strings.HasSuffix(origPath, "\\") ||
+		strings.HasSuffix(origPath, "/")
+
+	if len(cleanedPath) > 1 && hasTrailingSlash && inputOS == "windows" {
+		// for cleaned paths, / will turn to \\
+		return cleanedPath + "\\"
+	}
+	return cleanedPath
+}