diff --git a/lisp/cli/doctor.el b/lisp/cli/doctor.el
index 7802f2227..b45716e0c 100644
--- a/lisp/cli/doctor.el
+++ b/lisp/cli/doctor.el
@@ -169,21 +169,52 @@ in."
         (explain! "The second directory will be ignored, as it has lower precedence."))))
 
   (print! (start "Checking for common environmental issues..."))
-  (when (string-match-p "/fish$" shell-file-name)
-    (print! (warn "Detected Fish as your $SHELL"))
-    (explain! "Fish (and possibly other non-POSIX shells) is known to inject garbage "
-              "output into some of the child processes that Emacs spawns. Many Emacs "
-              "packages/utilities will choke on this output, causing unpredictable issues. "
-              "To get around this, either:\n\n"
-              "  - Add the following to $DOOMDIR/config.el:\n\n"
-              "    (setq shell-file-name (executable-find \"bash\"))\n\n"
-              "  - Or change your default shell to a POSIX shell (like bash or zsh) "
-              "    and explicitly configure your terminal apps to use the shell you "
-              "    want.\n\n"
-              "If you opt for option 1 and use one of Emacs' terminal emulators, you "
-              "will also need to configure them to use Fish, e.g.\n\n"
-              "  (setq-default vterm-shell (executable-find \"fish\"))\n\n"
-              "  (setq-default explicit-shell-file-name (executable-find \"fish\"))\n"))
+  (print-group!
+    (when (string-match-p "/fish$" shell-file-name)
+      (print! (warn "Detected Fish as your $SHELL"))
+      (explain! "Fish (and possibly other non-POSIX shells) is known to inject garbage "
+                "output into some of the child processes that Emacs spawns. Many Emacs "
+                "packages/utilities will choke on this output, causing unpredictable issues. "
+                "To get around this, either:\n\n"
+                "  - Add the following to $DOOMDIR/config.el:\n\n"
+                "    (setq shell-file-name (executable-find \"bash\"))\n\n"
+                "  - Or change your default shell to a POSIX shell (like bash or zsh) "
+                "    and explicitly configure your terminal apps to use the shell you "
+                "    want.\n\n"
+                "If you opt for option 1 and use one of Emacs' terminal emulators, you "
+                "will also need to configure them to use Fish, e.g.\n\n"
+                "  (setq-default vterm-shell (executable-find \"fish\"))\n\n"
+                "  (setq-default explicit-shell-file-name (executable-find \"fish\"))\n"))
+
+    (condition-case e
+        (when (featurep :system 'windows)
+          (let ((filea (expand-file-name "__testfile1" temporary-file-directory))
+                (fileb (expand-file-name "__testfile2" temporary-file-directory)))
+            (unwind-protect
+                (progn
+                  (with-temp-file fileb)
+                  (make-symbolic-link fileb filea)
+                  (not (file-symlink-p filea)))
+              (delete-file filea)
+              (delete-file fileb))))
+      ('file-error
+       (when (equal (cons (nth 1 e) (nth 2 e))
+                    (cons "Making symbolic link" "Operation not permitted"))
+         (print! (warn "Symlinks are not enabled on this operating system"))
+         (explain! "In the near future, Doom will make extensive use of symlinks to save space "
+                   "and simplify package and profile management. Without symlinks, much of it "
+                   "won't be functional. To get around this, you have three options:"
+                   "\n\n"
+                   "  - Enabling 'Developer Mode' in the Windows settings (search for 'Developer "
+                   "    Settings' in the start menu). This will warn you about its effect on system "
+                   "    security, but this can be ignored. If it bothers you, consider another option "
+                   "    below.\n"
+                   "  - Running your shell (cmd or powershell) in administrator mode anytime you "
+                   "    need to use the 'doom' script. Also, the `doom/reload' command won't work "
+                   "    unless Emacs itself is launched in administrator mode.\n"
+                   "  - Install Emacs in WSL 1/2; the native Linux environment it creates supports "
+                   "    symlinks out of the box and is the best option (as Emacs is generally more "
+                   "    stable, predictable, and faster there).\n\n")))))
 
   (print! (start "Checking for stale elc files..."))
   (elc-check-dir doom-core-dir)