diff --git a/core/defuns/defuns-spaceline.el b/core/defuns/defuns-spaceline.el
index da1f3d63f..b3975afcb 100644
--- a/core/defuns/defuns-spaceline.el
+++ b/core/defuns/defuns-spaceline.el
@@ -1,5 +1,8 @@
 ;;; defuns-spaceline.el
 
+(defvar doom-env-version-hook '()
+  "Hook that runs whenever the environment version changes (e.g. rbenv/pyenv)")
+
 ;;;###autoload
 (defun doom|spaceline-env-update ()
   (when doom--env-command
@@ -7,7 +10,8 @@
       (let ((s (shell-command-to-string doom--env-command)))
         (setq doom--env-version (if (string-match "[ \t\n\r]+\\'" s)
                                     (replace-match "" t t s)
-                                  s))))))
+                                  s))
+        (run-hook-with-args 'doom-env-version-hook doom--env-version)))))
 
 ;;;###autoload
 (defun doom/-flycheck-count (state)
diff --git a/modules/module-ruby.el b/modules/module-ruby.el
index be844ec7f..7069b4a7e 100644
--- a/modules/module-ruby.el
+++ b/modules/module-ruby.el
@@ -14,7 +14,11 @@
   (def-version-cmd! ruby-mode "ruby --version | cut -d' ' -f2")
   (setq ruby-deep-indent-paren t)
   ;; Don't interfere with my custom RET behavior
-  (define-key ruby-mode-map [?\n] nil))
+  (define-key ruby-mode-map [?\n] nil)
+
+  (add-hook 'doom-env-version-hook
+    (lambda (v) (when (eq major-mode 'ruby-mode)
+             (push (if (string-prefix-p "2" v) "Ruby_2" "Ruby") helm-dash-docsets)))))
 
 (use-package ruby-refactor
   :after ruby-mode