diff --git a/Lib/tarfile.py b/Lib/tarfile.py
index bd73965abf8..02858ae035a 100644
--- a/Lib/tarfile.py
+++ b/Lib/tarfile.py
@@ -2397,7 +2397,7 @@ class TarFile(object):
         """
         if tarinfo.issym():
             # Always search the entire archive.
-            linkname = os.path.dirname(tarinfo.name) + "/" + tarinfo.linkname
+            linkname = "/".join(filter(None, (os.path.dirname(tarinfo.name), tarinfo.linkname)))
             limit = None
         else:
             # Search the archive before the link, because a hard link is
diff --git a/Lib/test/test_tarfile.py b/Lib/test/test_tarfile.py
index d5b864e238b..a3685ea273a 100644
--- a/Lib/test/test_tarfile.py
+++ b/Lib/test/test_tarfile.py
@@ -154,6 +154,9 @@ class UstarReadTest(ReadTest):
     def test_fileobj_symlink2(self):
         self._test_fileobj_link("./ustar/linktest2/symtype", "ustar/linktest1/regtype")
 
+    def test_issue14160(self):
+        self._test_fileobj_link("symtype2", "ustar/regtype")
+
 
 class CommonReadTest(ReadTest):
 
diff --git a/Lib/test/testtar.tar b/Lib/test/testtar.tar
index bac0e2628f3..440182a437d 100644
Binary files a/Lib/test/testtar.tar and b/Lib/test/testtar.tar differ
diff --git a/Misc/NEWS b/Misc/NEWS
index 282a8eb265d..1e088c03e05 100644
--- a/Misc/NEWS
+++ b/Misc/NEWS
@@ -56,6 +56,9 @@ Core and Builtins
 Library
 -------
 
+- Issue #14160: TarFile.extractfile() failed to resolve symbolic links when
+  the links were not located in an archive subdirectory.
+
 - Issue #14638: pydoc now treats non-string __name__ values as if they
   were missing, instead of raising an error.