diff --git a/core/cli/autoloads.el b/core/cli/autoloads.el
index cfc03ba57..8150513c3 100644
--- a/core/cli/autoloads.el
+++ b/core/cli/autoloads.el
@@ -32,14 +32,16 @@ one wants that.")
      (cl-check-type file string)
      (and (print! (start "Generating core autoloads..."))
           (doom-cli--write-autoloads
-           file (doom-cli--generate-autoloads
-                 (cl-loop for dir
-                          in (append (list doom-core-dir)
-                                     (cdr (doom-module-load-path 'all-p))
-                                     (list doom-private-dir))
-                          if (doom-glob dir "autoload.el") collect it
-                          if (doom-glob dir "autoload/*.el") append it)
-                 'scan))
+           file
+           (doom-cli--generate-emacs-version-check)
+           (doom-cli--generate-autoloads
+            (cl-loop for dir
+                     in (append (list doom-core-dir)
+                                (cdr (doom-module-load-path 'all-p))
+                                (list doom-private-dir))
+                     if (doom-glob dir "autoload.el") collect it
+                     if (doom-glob dir "autoload/*.el") append it)
+            'scan))
           (print! (start "Byte-compiling core autoloads file..."))
           (doom-cli--byte-compile-file file)
           (print! (success "Generated %s")
@@ -105,6 +107,12 @@ one wants that.")
                 (print! "M-x doom/restart")
                 (print! "M-x doom/reload")))
 
+(defun doom-cli--generate-emacs-version-check ()
+  `((unless (equal emacs-major-version (eval-when-compile emacs-major-version))
+      (signal 'doom-error
+              (list "Your installed (major) version of Emacs has changed"
+                    "Run 'doom sync && doom build' to bring Doom up to speed")))))
+
 (defun doom-cli--generate-var-cache (vars)
   `((setq ,@(cl-loop for var in vars
                      append `(,var ',(symbol-value var))))))
diff --git a/core/core-lib.el b/core/core-lib.el
index 8abf49780..0dd055f72 100644
--- a/core/core-lib.el
+++ b/core/core-lib.el
@@ -101,6 +101,8 @@ Return t on success, nil otherwise (but logs a warning)."
       ;; `string-remove-suffix' is much cheaper (because it does no file sanity
       ;; checks during or after; just plain ol' string manipulation).
       (load (string-remove-suffix ".el" file) noerror 'nomessage)
+    (doom-error
+     (signal (car e) (cdr e)))
     ((debug error)
      (message "Autoload file error: %s -> %s" (file-name-nondirectory file) e)
      nil)))