diff --git a/modules/config/default/+evil-bindings.el b/modules/config/default/+evil-bindings.el
index 25b310960..3e993473e 100644
--- a/modules/config/default/+evil-bindings.el
+++ b/modules/config/default/+evil-bindings.el
@@ -436,19 +436,7 @@
         :n "gb"  #'git-timemachine-blame))
 
 ;;; :tools
-(map! (:when (featurep! :tools debugger)
-        :after realgud
-        :map realgud:shortkey-mode-map
-        :n "j" #'evil-next-line
-        :n "k" #'evil-previous-line
-        :n "h" #'evil-backward-char
-        :n "l" #'evil-forward-char
-        :n "c" #'realgud:cmd-continue
-        :m "n" #'realgud:cmd-next
-        :m "b" #'realgud:cmd-break
-        :m "B" #'realgud:cmd-clear)
-
-      (:when (featurep! :tools eval)
+(map! (:when (featurep! :tools eval)
         :g  "M-r" #'+eval/buffer
         :nv "gr"  #'+eval:region
         :n  "gR"  #'+eval/buffer
@@ -721,7 +709,7 @@
           :desc "Tags search"    "m"  #'org-tags-view
           :desc "View search"    "v"  #'org-search-view)
         :desc "Default browser"    "b"  #'browse-url-of-file
-        :desc "Debugger"           "d"  #'+debug/open
+        :desc "Start debugger"     "d"  #'+debugger/start
         :desc "REPL"               "r"  #'+eval/open-repl-other-window
         :desc "REPL (same window)" "R"  #'+eval/open-repl-same-window
         :desc "Dired"              "-"  #'dired-jump
diff --git a/modules/editor/evil/+commands.el b/modules/editor/evil/+commands.el
index a110e673d..263dce2db 100644
--- a/modules/editor/evil/+commands.el
+++ b/modules/editor/evil/+commands.el
@@ -177,7 +177,7 @@ If BANG, search Doom documentation."
 ;;; Project tools
 (evil-ex-define-cmd "compile"     #'+evil:compile)
 (evil-ex-define-cmd "mak[e]"      #'+evil:make)
-;; (evil-ex-define-cmd "debug"       #'+debug/run)
+(evil-ex-define-cmd "debug"       #'+debugger/start)
 (evil-ex-define-cmd "er[rors]"    #'flycheck-list-errors)
 
 ;;; File operations
diff --git a/modules/tools/debugger/autoload/debug.el b/modules/tools/debugger/autoload/debug.el
deleted file mode 100644
index 691ea909c..000000000
--- a/modules/tools/debugger/autoload/debug.el
+++ /dev/null
@@ -1,11 +0,0 @@
-;;; tools/debugger/autoload/debug.el -*- lexical-binding: t; -*-
-
-;;;###autoload
-(defun +debugger/quit ()
-  "Quit the active debugger, if any."
-  (interactive)
-  (ignore-errors (call-interactively #'realgud:cmd-quit))
-  (doom/popup-close)
-  (when (featurep 'evil)
-    (evil-normal-state)))
-
diff --git a/modules/tools/debugger/autoload/debugger.el b/modules/tools/debugger/autoload/debugger.el
new file mode 100644
index 000000000..24ad342eb
--- /dev/null
+++ b/modules/tools/debugger/autoload/debugger.el
@@ -0,0 +1,82 @@
+;;; tools/debugger/autoload/debugger.el -*- lexical-binding: t; -*-
+
+(defvar +debugger--last nil)
+
+(defun +debugger-list-for-dap ()
+  (when (and (bound-and-true-p lsp-mode)
+             (require 'dap-mode nil t)
+             dsp-mode)
+    (mapcar #'car dap--debug-template-configurations)))
+
+(defun +debugger-list-for-realgud ()
+  (cl-loop for (sym . plist) in +debugger-realgud-alist
+           for sym-name = (symbol-name sym)
+           for modes = (plist-get plist :modes)
+           if (or (null modes) (apply #'derived-mode-p modes))
+           collect sym))
+
+
+(defun +debugger-list-available ()
+  "TODO"
+  (append (+debugger-list-for-dap)
+          (+debugger-list-for-realgud)
+          nil))
+
+
+;;
+;;; Interactive commands
+
+;;;###autoload
+(defun +debugger/start-last ()
+  "Relaunch the last debugger session."
+  (interactive)
+  (unless +debugger--last
+    (user-error "No last debugger to invoke"))
+  (call-interactively +debugger--last))
+
+;;;###autoload
+(defun +debugger/start (arg)
+  "Launch a debugger session.
+
+Launches the last used debugger, if one exists. Otherwise, you will be prompted
+for what debugger to use. If the prefix ARG is set, prompt anyway."
+  (interactive "P")
+  (if (or arg (null +debugger--last))
+      (let ((debugger (intern-soft (completing-read "Start debugger: " (+debugger-list-available)))))
+        (unless debugger
+          (user-error "No debugging session to quit"))
+        (unless (fboundp debugger)
+          (user-error "Couldn't find debugger backend %S" debugger))
+        (setq-local +debugger--last debugger)
+        (call-interactively debugger))
+    (+debugger/start-last)))
+
+;;;###autoload
+(defun +debugger/quit ()
+  "Quit the active debugger, if any."
+  (interactive)
+  (cond ((and (fboundp 'dap--cur-session) (dap--cur-session))
+         (dap-disconnect))
+        ((and (fboundp 'realgud-get-cmdbuf) (realgud-get-cmdbuf))
+         (let ((buf (realgud-get-cmdbuf)))
+           (ignore-errors
+             (call-interactively #'realgud:cmd-quit))
+           (let (realgud-safe-mode)
+             (kill-buffer buf))))
+        ((user-error "No debugging session to quit"))))
+
+;; TODO debugger breakpoint commands
+;; ;;;###autoload
+;; (defun +debugger/toggle-breakpoint ()
+;;   (interactive)
+;;   (user-error "not implemented yet"))
+
+;; ;;;###autoload
+;; (defun +debugger/next-breakpoint ()
+;;   (interactive)
+;;   (user-error "not implemented yet"))
+
+;; ;;;###autoload
+;; (defun +debugger/previous-breakpoint ()
+;;   (interactive)
+;;   (user-error "not implemented yet"))
diff --git a/modules/tools/debugger/config.el b/modules/tools/debugger/config.el
index 7714f3a19..252cb1745 100644
--- a/modules/tools/debugger/config.el
+++ b/modules/tools/debugger/config.el
@@ -1,9 +1,31 @@
 ;;; tools/debugger/config.el -*- lexical-binding: t; -*-
 
+(defvar +debugger--realgud-alist
+  '((realgud:zshdb     :modes (sh-mode))
+    (realgud:kshdb     :modes (sh-mode))
+    (realgud:rdebug    :modes (ruby-mode enh-ruby-mode))
+    (realgud:pdb       :modes (python-mode))
+    (realgud:trepan2   :modes (python-mode))
+    (realgud:gub       :modes (go-mode))
+    (realgud:gdb)
+    (realgud:trepan    :modes (perl-mode perl6-mode))
+    (realgud:trepanpl  :modes (perl-mode perl6-mode))
+    (realgud:trepanjs  :modes (javascript-mode js2-mode js3-mode))
+    (realgud:remake)
+    (realgud:trepan3k  :modes (python-mode))
+    (realgud:bashdb    :modes (sh-mode))
+    (realgud:perldb    :modes (perl-mode perl6-mode))))
+
+
+;;
+;;; Packages
+
 (def-package! dap-mode
   :when (featurep! :tools lsp)
   :hook (dap-mode . dap-ui-mode)
   :after lsp-mode
+  :init
+  (setq dap--breakpoints-file (concat doom-etc-dir "dap-breakpoints"))
   :config
   (dap-mode 1)
   (dolist (module '(((:lang . java) lsp-java dap-java)
@@ -26,24 +48,35 @@
         (require 'dap-node)))))
 
 
-;; FIXME wildly outdated and untested; rewrite me!
 (def-package! realgud
-  :commands (realgud:gdb realgud:trepanjs realgud:bashdb realgud:zshdb)
+  :defer t
+  :init
+  (def-package! realgud-trepan-ni
+    :defer t
+    :init (add-to-list '+debugger--realgud-alist
+                       '(realgud:trepan-ni :modes (javascript-mode js2-mode js3-mode)
+                                           :package realgud-trepan-ni)))
+
+  ;; Realgud doesn't generate its autoloads properly so we do it ourselves
+  (dolist (debugger +debugger--realgud-alist)
+    (autoload (car debugger)
+      (if-let (sym (plist-get (cdr debugger) :package))
+          (symbol-name sym)
+        "realgud")
+      nil t))
+
   :config
-  (set-popup-rule! "^\\*\\(?:trepanjs:\\(?:g\\|zsh\\|bash\\)db\\)" :size 20)
+  (set-popup-rule! "^\\*\\(?:trepanjs:\\(?:g\\|zsh\\|bash\\)db\\|pdb \\)"
+    :size 20 :select nil :quit nil)
 
-  (when (featurep! :lang javascript)
-    (after! js2-mode
-      (require 'realgud-trepan-ni)))
-
-  ;; TODO Temporary Ex commands for the debugger
-  ;; (def-tmp-excmd! doom:def-debug-on doom:def-debug-off
-  ;;   ("n[ext]" . realgud:cmd-next)
-  ;;   ("s[tep]" . realgud:cmd-step)
-  ;;   ("b[reak]" . +debug:toggle-breakpoint)
-  ;;   ("c[ontinue]" . realgud:cmd-continue))
-  ;; (advice-add #'realgud-cmdbuf-init :after #'doom:def-debug-on)
-  ;; (advice-add #'realgud:cmd-quit :after #'doom:def-debug-off)
+  (defun +debugger*cleanup-when-realgud-terminates (&optional buf)
+    "Kill command buffer when debugging session ends (which closes its popup)."
+    (when (stringp buf)
+      (setq buf (get-buffer buf)))
+    (when-let (cmdbuf (realgud-get-cmdbuf buf))
+      (let (kill-buffer-hook)
+        (kill-buffer buf))))
+  (advice-add #'realgud:terminate :after #'+debugger*cleanup-when-realgud-terminates)
 
   ;; Monkey-patch `realgud:run-process' to run in a popup.
   ;; TODO Find a more elegant solution
@@ -55,7 +88,7 @@
            (process (get-buffer-process cmd-buf)))
       (cond ((and process (eq 'run (process-status process)))
              (pop-to-buffer cmd-buf)
-             (define-key evil-emacs-state-local-map (kbd "ESC ESC") #'+debug/quit)
+             (define-key evil-emacs-state-local-map (kbd "ESC ESC") #'+debugger/quit)
              (realgud:track-set-debugger debugger-name)
              (realgud-cmdbuf-info-in-debugger?= 't)
              (realgud-cmdbuf-info-cmd-args= cmd-args)
@@ -65,8 +98,11 @@
                  (let* ((info realgud-cmdbuf-info)
                         (cmd-args (realgud-cmdbuf-info-cmd-args info))
                         (cmd-str  (mapconcat #'identity cmd-args " ")))
+                   (if (boundp 'starting-directory)
+                       (realgud-cmdbuf-info-starting-directory= starting-directory))
                    (set minibuffer-history-var
-                        (list-utils-uniq (cons cmd-str (eval minibuffer-history-var))))))))
+                        (cl-remove-duplicates
+                         (cons cmd-str (eval minibuffer-history)) :from-end))))))
             (t
              (if cmd-buf (switch-to-buffer cmd-buf))
              (message "Error running command: %s" (mapconcat #'identity cmd-args " "))))