diff --git a/src/basic/path-util.c b/src/basic/path-util.c
index ab8674cd156..f59d4286273 100644
--- a/src/basic/path-util.c
+++ b/src/basic/path-util.c
@@ -369,7 +369,9 @@ char* path_simplify_full(char *path, PathSimplifyFlags flags) {
         if (isempty(path))
                 return path;
 
-        keep_trailing_slash = FLAGS_SET(flags, PATH_SIMPLIFY_KEEP_TRAILING_SLASH) && endswith(path, "/");
+        /* A trailing "/." is dropped below just like a trailing slash, but carries the same meaning
+         * (i.e. "this must be a directory"), hence turn it into a trailing slash too, if requested. */
+        keep_trailing_slash = FLAGS_SET(flags, PATH_SIMPLIFY_KEEP_TRAILING_SLASH) && ENDSWITH_SET(path, "/", "/.");
 
         absolute = path_is_absolute(path);
         f += absolute;  /* Keep leading /, if present. */
diff --git a/src/test/test-path-util.c b/src/test/test-path-util.c
index 89af3d6b63c..96d1482b81b 100644
--- a/src/test/test-path-util.c
+++ b/src/test/test-path-util.c
@@ -198,6 +198,13 @@ TEST(path_simplify) {
         test_path_simplify_one("/../abc///..", "/abc/..", PATH_SIMPLIFY_KEEP_TRAILING_SLASH);
         test_path_simplify_one("/../abc///../", "/abc/../", PATH_SIMPLIFY_KEEP_TRAILING_SLASH);
         test_path_simplify_one("/../abc///../", "/abc/..", /* flags= */ 0);
+        test_path_simplify_one("/abc/.", "/abc/", PATH_SIMPLIFY_KEEP_TRAILING_SLASH);
+        test_path_simplify_one("/abc/./", "/abc/", PATH_SIMPLIFY_KEEP_TRAILING_SLASH);
+        test_path_simplify_one("/abc//.//.", "/abc/", PATH_SIMPLIFY_KEEP_TRAILING_SLASH);
+        test_path_simplify_one("/abc/.", "/abc", /* flags= */ 0);
+        test_path_simplify_one("/.", "/", PATH_SIMPLIFY_KEEP_TRAILING_SLASH);
+        test_path_simplify_one("./.", "./", PATH_SIMPLIFY_KEEP_TRAILING_SLASH);
+        test_path_simplify_one(".", ".", PATH_SIMPLIFY_KEEP_TRAILING_SLASH);
 
         test_path_simplify_one("/../../abc", "/abc", PATH_SIMPLIFY_KEEP_TRAILING_SLASH);
         test_path_simplify_one("/../../abc///", "/abc/", PATH_SIMPLIFY_KEEP_TRAILING_SLASH);