diff --git a/winsup/cygwin/environ.cc b/winsup/cygwin/environ.cc
index 4e049211e9..955684e232 100644
--- a/winsup/cygwin/environ.cc
+++ b/winsup/cygwin/environ.cc
@@ -92,6 +92,8 @@ set_winsymlinks (const char *buf)
 			? WSYM_nativestrict : WSYM_native;
   else if (ascii_strncasematch (buf, "deepcopy", 8))
     allow_winsymlinks = WSYM_deepcopy;
+  else if (ascii_strncasematch (buf, "nativeordeepcopy", 8))
+    allow_winsymlinks = WSYM_native_or_deepcopy;
   else
     allow_winsymlinks = WSYM_sysfile;
 }
diff --git a/winsup/cygwin/globals.cc b/winsup/cygwin/globals.cc
index ab2c205609..f05bdb753e 100644
--- a/winsup/cygwin/globals.cc
+++ b/winsup/cygwin/globals.cc
@@ -57,7 +57,8 @@ enum winsym_t
   WSYM_nativestrict,
   WSYM_nfs,
   WSYM_sysfile,
-  WSYM_deepcopy
+  WSYM_deepcopy,
+  WSYM_native_or_deepcopy
 };
 
 exit_states NO_COPY exit_state;
diff --git a/winsup/cygwin/path.cc b/winsup/cygwin/path.cc
index 8806e59c7d..0d912e26a3 100644
--- a/winsup/cygwin/path.cc
+++ b/winsup/cygwin/path.cc
@@ -2110,6 +2110,9 @@ symlink_worker (const char *oldpath, path_conv &win32_newpath, bool isdevice)
       else if ((wsym_type == WSYM_native || wsym_type == WSYM_nativestrict)
 	       && !(win32_newpath.fs_flags () & FILE_SUPPORTS_REPARSE_POINTS))
 	wsym_type = WSYM_default;
+      else if (wsym_type == WSYM_native_or_deepcopy
+	       && !(win32_newpath.fs_flags () & FILE_SUPPORTS_REPARSE_POINTS))
+	wsym_type = WSYM_deepcopy;
 
       /* Attach .lnk suffix when shortcut is requested. */
       if (wsym_type == WSYM_lnk && !win32_newpath.exists ()
@@ -2144,6 +2147,7 @@ symlink_worker (const char *oldpath, path_conv &win32_newpath, bool isdevice)
 	  __leave;
 	case WSYM_native:
 	case WSYM_nativestrict:
+	case WSYM_native_or_deepcopy:
 	  res = symlink_native (oldpath, win32_newpath);
 	  if (!res)
 	    __leave;
@@ -2154,6 +2158,12 @@ symlink_worker (const char *oldpath, path_conv &win32_newpath, bool isdevice)
 	      __seterrno ();
 	      __leave;
 	    }
+	  /* With deepcopy fall back? Let's do that, then */
+	  if (res == -1 && wsym_type == WSYM_native_or_deepcopy)
+	    {
+	      wsym_type = WSYM_deepcopy;
+	      break;
+	    }
 	  /* Otherwise, fall back to default symlink type. */
 	  wsym_type = WSYM_default;
 	  fallthrough;
diff --git a/winsup/doc/cygwinenv.xml b/winsup/doc/cygwinenv.xml
index c4e9f3f9e7..754a9c1cfb 100644
--- a/winsup/doc/cygwinenv.xml
+++ b/winsup/doc/cygwinenv.xml
@@ -104,7 +104,7 @@ back to the parent process.</para>
 </listitem>
 
 <listitem>
-<para><envar>winsymlinks:{lnk,native,nativestrict,sys,deepcopy}</envar></para>
+<para><envar>winsymlinks:{lnk,native,nativestrict,sys,deepcopy,nativeordeepcopy}</envar></para>
 
 <itemizedlist mark="square">
 <listitem>
@@ -141,6 +141,14 @@ the source directory will be copied recursively). This mode makes a trade-off
 between compatibility and interoperability with Win32 programs, favoring the
 latter.</para>
 </listitem>
+
+<listitem>
+<para>If set to <literal>winsymlinks:nativeordeepcopy</literal> Cygwin creates
+symlinks as native Windows symlinks if supported (i.e. on file systems
+supporting symbolic links, and when the current user is permitted to create
+symbolic links, e.g. in Windows 10's "Developer Mode"), and fall back to
+creating a deep copy in case symlinks are not supported.</para>
+</listitem>
 </itemizedlist>
 
 <para>Note that this setting has no effect where Cygwin knows that the