diff --git a/collects/drracket/private/interface.rkt b/collects/drracket/private/interface.rkt
index 812b1ba166..007438bb57 100644
--- a/collects/drracket/private/interface.rkt
+++ b/collects/drracket/private/interface.rkt
@@ -54,6 +54,7 @@ remain the same for tools that use them.
     register-toolbar-button
     register-toolbar-buttons
     unregister-toolbar-button
+    sort-toolbar-buttons-panel
     get-tabs))
 
 (define unit:definitions-text<%> 
diff --git a/collects/drracket/private/module-language-tools.rkt b/collects/drracket/private/module-language-tools.rkt
index 58725a7e16..61825fbfd6 100644
--- a/collects/drracket/private/module-language-tools.rkt
+++ b/collects/drracket/private/module-language-tools.rkt
@@ -21,35 +21,42 @@
           [prefix drracket: drracket:interface^])
   (export drracket:module-language-tools^)
 
-  (define-struct opt-out-toolbar-button (make-button id) #:transparent)
+  (define-struct opt-out-toolbar-button (make-button id number) #:transparent)
   (define opt-out-toolbar-buttons '())
   
-  (define (add-opt-out-toolbar-button make-button id) 
+  (define (add-opt-out-toolbar-button make-button id #:number [number #f]) 
     (set! opt-out-toolbar-buttons
-          (cons (make-opt-out-toolbar-button make-button id)
+          (cons (make-opt-out-toolbar-button make-button id number)
                 opt-out-toolbar-buttons)))
     
+  (define-local-member-name
+    set-lang-toolbar-buttons
+    get-lang-toolbar-buttons)
+    
   (define tab-mixin
     (mixin (drracket:unit:tab<%>) (drracket:module-language-tools:tab<%>)
       (inherit get-frame)
       (define toolbar-buttons '())
       (define/public (get-lang-toolbar-buttons) toolbar-buttons)
-      (define/public (set-lang-toolbar-buttons bs)
+      (define/public (set-lang-toolbar-buttons bs ns)
         (for-each
          (λ (old-button) (send (get-frame) remove-toolbar-button old-button))
          toolbar-buttons)
         (set! toolbar-buttons bs)
-        (send (get-frame) register-toolbar-buttons toolbar-buttons)
+        (send (get-frame) register-toolbar-buttons toolbar-buttons #:numbers ns)
         (send (get-frame) when-initialized
               (λ ()
                 (send (send (get-frame) get-toolbar-button-panel) change-children
-                      (λ (l) toolbar-buttons)))))
+                      (λ (l) toolbar-buttons))))
+        (send (get-frame) sort-toolbar-buttons-panel))
       (super-new)))
   
   (define frame-mixin
     (mixin (drracket:unit:frame<%>) (drracket:module-language-tools:frame<%>)
-      (inherit unregister-toolbar-button get-definitions-text)
-  
+      (inherit unregister-toolbar-button 
+               get-definitions-text
+               sort-toolbar-buttons-panel)
+      
       (define toolbar-button-panel #f)
       (define/public (when-initialized thunk) 
         (cond
@@ -65,20 +72,19 @@
       (define/public (get-toolbar-button-panel) toolbar-button-panel)
       (define/public (remove-toolbar-button button)
         (send toolbar-button-panel change-children (λ (l) (remq button l)))
-        (unregister-toolbar-button button))
+        (unregister-toolbar-button button)
+        (sort-toolbar-buttons-panel))
       (define/augment (on-tab-change old-tab new-tab)
         (inner (void) on-tab-change old-tab new-tab)
         (when toolbar-button-panel
           (send toolbar-button-panel change-children
-                (λ (l) (send new-tab get-lang-toolbar-buttons)))))
+                (λ (l) (send new-tab get-lang-toolbar-buttons)))
+          (sort-toolbar-buttons-panel)))
       (super-new)
       (inherit get-button-panel)
       (set! toolbar-button-panel (new horizontal-panel% 
                                       [parent (get-button-panel)]
                                       [stretchable-width #f]))
-      ;; move button panel to the front of the list
-      (send (get-button-panel) change-children 
-            (λ (l) (cons toolbar-button-panel (remq toolbar-button-panel l))))
       (after-initialized)
       (set! after-initialized void)
       
@@ -184,9 +190,13 @@
                           'drracket/private/module-language-tools))
               (when info-result
                 (register-new-buttons
-                 (ctc-on-info-proc-result (or/c #f (listof (list/c string?
-                                                                   (is-a?/c bitmap%)
-                                                                   (-> (is-a?/c drracket:unit:frame<%>) any))))
+                 (ctc-on-info-proc-result (or/c #f (listof (or/c (list/c string?
+                                                                         (is-a?/c bitmap%)
+                                                                         (-> (is-a?/c drracket:unit:frame<%>) any))
+                                                                 (list/c string?
+                                                                         (is-a?/c bitmap%)
+                                                                         (-> (is-a?/c drracket:unit:frame<%>) any)
+                                                                         (or/c real? #f)))))
                                           (or (info-proc 'drracket:toolbar-buttons #f)
                                               (info-proc 'drscheme:toolbar-buttons #f)))
                  (ctc-on-info-proc-result (or/c #f (listof symbol?))
@@ -196,6 +206,15 @@
       (inherit get-tab)
       
       (define/private (register-new-buttons buttons opt-out-ids)
+        ;; cleaned-up-buttons : (listof (list/c string? (is-a?/c bitmap%) (-> (is-a?/c drracket:unit:frame<%>) any) (or/c real? #f)))
+        (define cleaned-up-buttons
+          (cond
+            [(not buttons) '()]
+            [else
+             (for/list ([button (in-list buttons)])
+               (if (= 3 (length button))
+                   (append button (list #f))
+                   button))]))
         (let* ([tab (get-tab)]
                [frame (send tab get-frame)])
           (send frame when-initialized
@@ -203,7 +222,7 @@
                   (send frame begin-container-sequence)
                   
                   ;; avoid any time with both sets of buttons in the panel so the window doesn't get too wide
-                  (send (send frame get-toolbar-button-panel) change-children (λ (x) '()))
+                  (send (send frame get-toolbar-button-panel) change-children (λ (prev) '()))
                   
                   (let ([directly-specified-buttons
                          (map (λ (button-spec)
@@ -214,25 +233,27 @@
                                      [callback
                                       (lambda (button)
                                         ((list-ref button-spec 2) frame))]))
-                              (or buttons '()))]
-                        [opt-out-buttons
+                              cleaned-up-buttons)]
+                        [directly-specified-button-numbers (map (λ (button-spec) (list-ref button-spec 3)) 
+                                                                cleaned-up-buttons)]
+                        [opt-out-buttons+numbers
                          (if (eq? opt-out-ids #f)
                              '()
                              (map
                               (λ (opt-out-toolbar-button)
-                                ((opt-out-toolbar-button-make-button opt-out-toolbar-button) 
-                                 frame
-                                 (send frame get-toolbar-button-panel)))
+                                (list ((opt-out-toolbar-button-make-button opt-out-toolbar-button) 
+                                       frame
+                                       (send frame get-toolbar-button-panel))
+                                      (opt-out-toolbar-button-number opt-out-toolbar-button)))
                               (filter (λ (opt-out-toolbar-button)
                                         (not (member (opt-out-toolbar-button-id opt-out-toolbar-button) 
                                                      opt-out-ids)))
                                       opt-out-toolbar-buttons)))])
                     (send tab set-lang-toolbar-buttons
-                          (sort
-                           (append directly-specified-buttons
-                                   opt-out-buttons)
-                           string<=?
-                           #:key (λ (x) (send x get-label)))))
+                          (append directly-specified-buttons
+                                  (map (λ (x) (list-ref x 0)) opt-out-buttons+numbers))
+                          (append directly-specified-button-numbers
+                                  (map (λ (x) (list-ref x 1)) opt-out-buttons+numbers))))
                   (send frame end-container-sequence)))))
       
       (inherit get-text)
@@ -247,7 +268,7 @@
 
       ;; removes language-specific customizations
       (define/private (clear-things-out)
-        (send (get-tab) set-lang-toolbar-buttons '()))
+        (send (get-tab) set-lang-toolbar-buttons '() '()))
       
       (define/augment (after-set-next-settings settings)
         (update-in-module-language?
diff --git a/collects/drracket/private/syncheck/gui.rkt b/collects/drracket/private/syncheck/gui.rkt
index e3679a23f2..5f691bd855 100644
--- a/collects/drracket/private/syncheck/gui.rkt
+++ b/collects/drracket/private/syncheck/gui.rkt
@@ -181,7 +181,8 @@ If the namespace does not, they are colored the unbound color.
               (alternate-bitmap syncheck-small-bitmap)
               (parent parent)
               (callback (λ (button) (send frame syncheck:button-callback)))))
-       'drracket:syncheck)
+       'drracket:syncheck
+       #:number 50)
       (drracket:unit:add-to-program-editor-mixin clearing-text-mixin))
     (define (phase2) (void))
     
@@ -1544,15 +1545,17 @@ If the namespace does not, they are colored the unbound color.
         
         (define/private (update-button-visibility/tab tab)
           (update-button-visibility/settings (send (send tab get-defs) get-next-settings)))
+        (inherit sort-toolbar-buttons-panel)
         (define/public (update-button-visibility/settings settings)
           (let* ([lang (drracket:language-configuration:language-settings-language settings)]
                  [visible? (and (not (is-a? lang drracket:module-language:module-language<%>))
                                 (send lang capability-value 'drscheme:check-syntax-button))])
-            (send check-syntax-button-parent-panel change-children
+            (send (get-button-panel) change-children
                   (λ (l)
                     (if visible?
-                        (list check-syntax-button)
-                        '())))))
+                        (cons check-syntax-button (remq check-syntax-button l))
+                        (remq check-syntax-button l))))
+            (sort-toolbar-buttons-panel)))
         
         ;; set-syncheck-running-mode : (or/c (box boolean?) 'button #f) -> boolean
         ;; records how a particular check syntax is being played out in the editor right now.
@@ -2037,25 +2040,16 @@ If the namespace does not, they are colored the unbound color.
                 
         (super-new)
         
-        (define check-syntax-button-parent-panel 
-          (new horizontal-panel%
-               [parent (get-button-panel)]
-               [stretchable-width #f]
-               [stretchable-height #f]))
         (define check-syntax-button
           (new switchable-button%
-               (label (string-constant check-syntax))
-               (bitmap syncheck-bitmap)
-               (alternate-bitmap syncheck-small-bitmap)
-               (parent check-syntax-button-parent-panel)
-               (callback (λ (button) (syncheck:button-callback)))))
+               [label (string-constant check-syntax)]
+               [bitmap syncheck-bitmap]
+               [alternate-bitmap syncheck-small-bitmap]
+               [parent (get-button-panel)]
+               [callback (λ (button) (syncheck:button-callback))]))
         (inherit register-toolbar-button)
-        (register-toolbar-button check-syntax-button)
+        (register-toolbar-button check-syntax-button #:number 50)
         (define/public (syncheck:get-button) check-syntax-button)
-        (send (get-button-panel) change-children
-              (λ (l)
-                (cons check-syntax-button-parent-panel
-                      (remove check-syntax-button-parent-panel l))))
         (update-button-visibility/tab (get-current-tab))))
     
     (define report-error-style (make-object style-delta% 'change-style 'italic))
diff --git a/collects/drracket/private/unit.rkt b/collects/drracket/private/unit.rkt
index ec058b7bc4..5525d24bf1 100644
--- a/collects/drracket/private/unit.rkt
+++ b/collects/drracket/private/unit.rkt
@@ -1886,12 +1886,11 @@ module browser threading seems wrong.
               (when (or (is-a? obj vertical-panel%)
                         (is-a? obj horizontal-panel%))
                 (unless (equal? (send obj get-orientation) (not vertical?))
-                  (send obj set-orientation (not vertical?))
-                  ;; have to be careful to avoid reversing the list when the orientation is already proper
-                  (send obj change-children reverse)))
+                  (send obj set-orientation (not vertical?))))
               (for-each loop (send obj get-children))))
+          (sort-toolbar-buttons-panel)
           
-          (orient)
+          (set-toolbar-label-visibilities/check-registered)
           
           (send top-outer-panel stretchable-height vertical?)
           (send top-outer-panel stretchable-width (not vertical?))
@@ -1918,31 +1917,102 @@ module browser threading seems wrong.
               (send name-panel set-alignment 'left 'center))
           (end-container-sequence)))
       
-      (define toolbar-buttons '())
-      (define/public (register-toolbar-button b)
-        (set! toolbar-buttons (cons b toolbar-buttons))
-        (orient))
+      ;; this table uses object identity on buttons(!)
+      (define toolbar-buttons (make-hasheq))
+      (define smallest #f)
       
-      (define/public (register-toolbar-buttons bs)
-        (set! toolbar-buttons (append bs toolbar-buttons))
-        (orient))
+      (define/public (register-toolbar-button b #:number [number/f #f])
+        (add-to-toolbar-buttons 'register-toolbar-button b number/f)
+        (set-toolbar-label-visibilities/check-registered)
+        (sort-toolbar-buttons-panel))
+      
+      (define/public (register-toolbar-buttons bs #:numbers [numbers/fs (make-list (length bs) #f)])
+        (for ([b (in-list bs)]
+              [n (in-list numbers/fs)]) 
+          (add-to-toolbar-buttons 'register-toolbar-buttons b n))
+        (set-toolbar-label-visibilities/check-registered)
+        
+        ;; sort panel contents
+        (define panels '())
+        (for ([tb (in-list bs)])
+          (define parent (send tb get-parent))
+          (unless (memq parent panels)
+            (set! panels (cons parent panels))))
+        (for ([panel (in-list panels)])
+          (sort-toolbar-buttons-panel)))
+      
+      (define/private (add-to-toolbar-buttons who button number/f)
+        (define number (or number/f (if smallest (- smallest 1) 100)))
+        (define prev (hash-ref toolbar-buttons button #f))
+        (when (and prev (not (= prev number)))
+          (error who "cannot add toolbar button ~s with number ~a; already added with ~a"
+                 (send button get-label)
+                 number
+                 prev))
+        (when (or (not smallest) (< number smallest))
+          (set! smallest number))
+        (hash-set! toolbar-buttons button number))
+      
+      (define/private (in-toolbar-list? b) (hash-ref toolbar-buttons b #f))
       
       (define/public (unregister-toolbar-button b)
-        (set! toolbar-buttons (remq b toolbar-buttons))
+        (hash-remove! toolbar-buttons b)
+        (set! smallest
+              (if (zero? (hash-count toolbar-buttons))
+                  #f
+                  (apply min (hash-map toolbar-buttons (λ (x y) y)))))
         (void))
       
-      (define/private (orient)
+      (define/public (sort-toolbar-buttons-panel)
+        (define bp (get-button-panel))
+        (when (is-a? bp panel%)
+          (let sort-loop ([panel bp])
+            (define min #f)
+            (send panel change-children
+                  (λ (l)
+                    (define sub-panel-nums (make-hash))
+                    (for ([x (in-list l)])
+                      (when (is-a? x area-container<%>)
+                        (hash-set! sub-panel-nums x (sort-loop x))))
+                    (define (key i)
+                      (or (let loop ([item i])
+                            (cond
+                              [(is-a? item area-container<%>)
+                               (hash-ref sub-panel-nums item)]
+                              [else
+                               (hash-ref toolbar-buttons item #f)]))
+                          -5000))
+                    (define (min/f a b)
+                      (cond
+                        [(and a b) (min a b)]
+                        [else (or a b)]))
+                    (define cmp
+                      (cond
+                        [(is-a? panel vertical-pane%) >=]
+                        [(is-a? panel horizontal-pane%) <=]
+                        [else
+                         (if (send panel get-orientation) ;; horizontal is #t
+                             <=
+                             >=)]))
+                    (define ans (sort l cmp #:key key))
+                    (set! min (if (null? ans)
+                                  #f
+                                  (key (car ans))))
+                    ans))
+            min)
+          (void)))
+
+      (define/private (set-toolbar-label-visibilities/check-registered)
         (let ([vertical? (or (toolbar-is-left?) (toolbar-is-right?))])
-          (for-each
-           (λ (obj) (send obj set-label-visible (not vertical?)))
-           toolbar-buttons))
+          (for ([(button number) (in-hash toolbar-buttons)])
+            (send button set-label-visible (not vertical?))))
         
         (let loop ([obj button-panel])
           (cond
             [(is-a? obj area-container<%>)
              (for-each loop (send obj get-children))]
             [(is-a? obj switchable-button%)
-             (unless (memq obj toolbar-buttons)
+             (unless (in-toolbar-list? obj)
                (error 'register-toolbar-button 
                       "found a switchable-button% that is not registered, label ~s"
                       (send obj get-label)))]
@@ -4293,7 +4363,7 @@ module browser threading seems wrong.
                  [callback (λ (x) (execute-callback))]
                  [bitmap execute-bitmap]
                  [label (string-constant execute-button-label)]))
-      (register-toolbar-button execute-button)
+      (register-toolbar-button execute-button #:number 100)
       
       (set! break-button
             (new switchable-button%
@@ -4301,7 +4371,7 @@ module browser threading seems wrong.
                  [callback (λ (x) (send current-tab break-callback))]
                  [bitmap break-bitmap]
                  [label (string-constant break-button-label)]))
-      (register-toolbar-button break-button)
+      (register-toolbar-button break-button #:number 101)
       
       (send button-panel stretchable-height #f)
       (send button-panel stretchable-width #f) 
diff --git a/collects/drracket/tool-lib.rkt b/collects/drracket/tool-lib.rkt
index b9e772b48a..fefcca2d8b 100644
--- a/collects/drracket/tool-lib.rkt
+++ b/collects/drracket/tool-lib.rkt
@@ -87,18 +87,22 @@ all of the names in the tools library, for use defining keybindings
  
  (proc-doc/names
   drracket:module-language-tools:add-opt-out-toolbar-button
-  (-> (-> (is-a?/c top-level-window<%>)
-          (is-a?/c area-container<%>) 
-          (is-a?/c switchable-button%))
-      symbol?
-      void?)
-  (make-button id)
+  (->* ((-> (is-a?/c top-level-window<%>)
+            (is-a?/c area-container<%>) 
+            (is-a?/c switchable-button%))
+        symbol?)
+       (#:number (or/c real? #f))
+       void?)
+  ((make-button id) ((number #f)))
   @{Call this function to add another button to DrRacket's toolbar. When buttons are added this way,
     DrRacket monitors the @tt{#lang} line at the top of the file; when it changes DrRacket queries
     the language to see if this button should be included.
     These buttons are ``opt out'', meaning that if the language doesn't explicitly ask to not
     have this button (or all such buttons), the button will appear.
     
+    The @racket[number] argument is the same as the @racket[number] argument
+    to @method[drracket:unit:frame<%> register-toolbar-button].
+
     @language-info-def[drracket:opt-out-toolbar-buttons]{
       See @racket[read-language] for more details on how a language can opt out.
       DrRacket will invoke the @tt{get-info} proc from @racket[read-language] with
diff --git a/collects/gui-debugger/debug-tool.rkt b/collects/gui-debugger/debug-tool.rkt
index 1cffd8db69..52a7f41ef3 100644
--- a/collects/gui-debugger/debug-tool.rkt
+++ b/collects/gui-debugger/debug-tool.rkt
@@ -1382,7 +1382,7 @@
       		      [alignment '(center center)]))
                (callback (λ (button) (debug-callback)))))
         (inherit register-toolbar-button)
-        (register-toolbar-button debug-button)
+        (register-toolbar-button debug-button #:number 60)
 
         (define/augment (enable-evaluation)
           (send debug-button enable #t)
diff --git a/collects/handin-client/client-gui.rkt b/collects/handin-client/client-gui.rkt
index a97a9cd67a..3912a64740 100644
--- a/collects/handin-client/client-gui.rkt
+++ b/collects/handin-client/client-gui.rkt
@@ -806,7 +806,7 @@
                                    get-editor)))])))]))
 
         (inherit register-toolbar-button)
-        (register-toolbar-button client-button)
+        (register-toolbar-button client-button #:number -1000)
 
         (send (get-button-panel) change-children
               (lambda (l) (cons client-panel (remq client-panel l))))))
diff --git a/collects/macro-debugger/tool.rkt b/collects/macro-debugger/tool.rkt
index ca292e5256..191ec91746 100644
--- a/collects/macro-debugger/tool.rkt
+++ b/collects/macro-debugger/tool.rkt
@@ -102,7 +102,8 @@
                (alternate-bitmap small-macro-debugger-bitmap)
                (parent parent)
                (callback (lambda (button) (send frame run-macro-stepper)))))
-       'macro-stepper)
+       'macro-stepper
+       #:number 70)
       (drracket:language:register-capability
        'macro-stepper:enabled
        boolean?
@@ -138,7 +139,7 @@
                (parent macro-debug-panel)
                (callback (lambda (button) (run-macro-stepper)))))
         (inherit register-toolbar-button)
-        (register-toolbar-button macro-debug-button)
+        (register-toolbar-button macro-debug-button #:number 70)
 
         (define/augment (enable-evaluation)
           (send macro-debug-button enable #t)
diff --git a/collects/scribble/tools/drracket-buttons.rkt b/collects/scribble/tools/drracket-buttons.rkt
index 1df2a30893..ad531d8147 100644
--- a/collects/scribble/tools/drracket-buttons.rkt
+++ b/collects/scribble/tools/drracket-buttons.rkt
@@ -19,7 +19,7 @@
 
 (define original-error-display-handler (error-display-handler))
 
-(define (make-render-button label bmp mode suffix)
+(define (make-render-button label bmp mode suffix number)
   (list 
    label
    bmp
@@ -54,15 +54,16 @@
                                  (system (format "open \"~a\"" (path->string (path-replace-suffix fn suffix)))))])))]) 
           (send drs-frame execute-callback))]
        [else
-        (message-box "Scribble" "Cannot render buffer without filename")]))))
+        (message-box "Scribble" "Cannot render buffer without filename")]))
+   number))
 
 (define drracket-buttons
   (let ([html-button
-         (make-render-button "Scribble HTML" html.png "--html" #".html")]
+         (make-render-button "Scribble HTML" html.png "--html" #".html" 99)]
         [pdf-button
          ;; only available on OSX currently
          ;; when we have a general way of opening pdfs, can use that
-         (make-render-button "Scribble PDF" pdf.png "--pdf" #".pdf")])
+         (make-render-button "Scribble PDF" pdf.png "--pdf" #".pdf" 98)])
     (case (system-type)
       [(macosx) (list html-button pdf-button)]
       [else (list html-button)])))
diff --git a/collects/scribblings/tools/example-src.rkt b/collects/scribblings/tools/example-src.rkt
index 9cc9108b8d..4d5651a4bc 100644
--- a/collects/scribblings/tools/example-src.rkt
+++ b/collects/scribblings/tools/example-src.rkt
@@ -106,7 +106,7 @@
                                                 (get-definitions-text)))]
                                    [parent (get-button-panel)]
                                    [bitmap reverse-content-bitmap])])
-                         (register-toolbar-button btn)
+                         (register-toolbar-button btn #:number 11)
                          (send (get-button-panel) change-children
                                (λ (l)
                                  (cons btn (remq btn l)))))))
diff --git a/collects/scribblings/tools/module-language-tools.scrbl b/collects/scribblings/tools/module-language-tools.scrbl
index 569671d45d..617d07e8b7 100644
--- a/collects/scribblings/tools/module-language-tools.scrbl
+++ b/collects/scribblings/tools/module-language-tools.scrbl
@@ -14,11 +14,15 @@ Specifically, DrRacket will pass @indexed-racket['drracket:toolbar-buttons]
 to the function and expect back a value matching this contract:
 @racketblock[(or/c (listof (list/c string?
                                    (is-a?/c bitmap%)
-                                   (-> (is-a?/c drracket:unit:frame<%>) any)))
+                                   (-> (is-a?/c drracket:unit:frame<%>) any)
+                                   (or/c real? #f)))
                    #f)]
 which is then used to create new toolbar buttons, one for each list in the
 first. The string is the label on the button; the bitmap is the icon 
-(it should be 16x16), and the function is called when the button is clicked.
+(it should be 16x16); the function is called when the button is clicked;
+and the number is passed as the @racket[#:number] argument to
+@method[drracket:unit:frame<%> register-toolbar-button].
+
 If the result is @racket[#f], then no toolbar buttons are created.
 
 To implement functionality similar to the Run button, call the
@@ -28,6 +32,8 @@ want to use the @racket[drracket:rep:after-expression] parameter.
 If @racket['drracket:toolbar-buttons] is not recognized, DrRacket will also
 pass @indexed-racket['drscheme:toolbar-buttons]; this is for backwards
 compatibility and new code should not use it.
+Similarly, if the fourth element from the list (the argument to @racket[#:number])
+is not present, then it is treated as @racket[#f].
 
 
 @(tools-include "module-language-tools")
diff --git a/collects/scribblings/tools/unit.scrbl b/collects/scribblings/tools/unit.scrbl
index b7b293fe4e..f7ed5f5a05 100644
--- a/collects/scribblings/tools/unit.scrbl
+++ b/collects/scribblings/tools/unit.scrbl
@@ -724,16 +724,54 @@ Note that the capability must be registered separately, via
 
 }
 
-@defmethod[(register-toolbar-button [tb (is-a?/c switchable-button%)]) void?]{
-Registers the toolbar button @racket[tb]. This is required
+@defmethod[(register-toolbar-button
+            [tb (is-a?/c switchable-button%)]
+            [#:number num (or/c #f real?) #f])
+           void?]{
+Registers the toolbar button @racket[tb]. 
+
+The @racket[num] argument controls the ordering of @racket[tb]
+with respect to other toolbar buttons. If it is
+@racket[#f], then a number one smaller than the currently
+smallest number is used.
+
+The buttons are sorted by their numbers, from left to right
+in horizontal mode and from top to bottom in vertical mode.
+If buttons are in sub-panels they cannot, in general, be
+sorted entirely by number without changing the panel 
+structure, but when a sub-panel appears as a sibling of
+some toolbar buttons, the sorting routine looks for the smallest
+number appearing in a button in the sub-panel, and uses that
+number when sorting the panel that appears with the buttons.
+
+A number of buttons already come with numbers:
+the @onscreen{Stop} button's number is @racket[101], 
+the @onscreen{Run} button's number is @racket[100],
+the @onscreen{Scribble PDF} button's number is @racket[99],
+the @onscreen{Scribble HTML} button's number is @racket[98],
+the @onscreen{Macro Stepper} button's number is @racket[70],
+the @onscreen{Debug} button's number is @racket[60],
+the @onscreen{Stepper} button's number is @racket[59], and
+the @onscreen{Check Syntax} button's number is @racket[50].
+
+All three are children of the panel returned by
+@method[drracket:unit:frame% get-button-panel].
+
+Registration is required
 so that the toolbar buttons properly switch orientation when 
-the toolbar's position is moved.
+the toolbar's position is moved and the ordering via the
+@racket[number] argument is preserved. 
+See also @method[drracket:unit:frame<%> sort-toolbar-buttons-panel].
 }
 
-@defmethod[(register-toolbar-buttons [tbs (listof (is-a?/c switchable-button%))]) void?]{
-Simultaneously registers the toolbar buttons @racket[tbs]. This is required
-so that the toolbar buttons properly switch orientation when 
-the toolbar's position is moved.
+@defmethod[(register-toolbar-buttons 
+            [tbs (listof (is-a?/c switchable-button%))]
+            [#:numbers nums (listof (or/c real? #f)) (make-list (length tbs) #f)])
+           void?]{
+Simultaneously registers the toolbar buttons @racket[tbs].
+                                             
+See also @method[drracket:unit:frame<%> register-toolbar-button].
+
 }
 
 @defmethod[(unregister-toolbar-button [tb (is-a?/c switchable-button%)]) void?]{
@@ -741,6 +779,12 @@ Unregisters the toolbar button @racket[tb]. Use this method to ensure
 that the button is not referenced by this frame and thus can be gc'd.
 }
 
+@defmethod[(sort-toolbar-buttons-panel) void?]{
+  Sorts the children of @method[drracket:unit:frame% get-button-panel], 
+  according to the @racket[number] argument passed to
+  @method[drracket:unit:frame<%> register-toolbar-button].
+}
+
 }
 
 
diff --git a/collects/stepper/stepper-tool.rkt b/collects/stepper/stepper-tool.rkt
index 85c0b3bcb8..6c95660e7b 100644
--- a/collects/stepper/stepper-tool.rkt
+++ b/collects/stepper/stepper-tool.rkt
@@ -186,7 +186,7 @@
              [callback (lambda (dont-care) (send (get-current-tab)
                                                  stepper-button-callback))]))
       
-      (register-toolbar-button stepper-button)
+      (register-toolbar-button stepper-button #:number 59)
       
       (define (stepper-button-show)
         (unless (send stepper-button is-shown?)
diff --git a/doc/release-notes/drracket/HISTORY.txt b/doc/release-notes/drracket/HISTORY.txt
index 958d573552..bd0b6ba617 100644
--- a/doc/release-notes/drracket/HISTORY.txt
+++ b/doc/release-notes/drracket/HISTORY.txt
@@ -1,3 +1,10 @@
+------------------------------
+       Version 5.2.2
+------------------------------
+
+  . DrRacket's toolbar buttons now have numbers associated with them
+    to control what order they appear in.
+
 ------------------------------
        Version 5.2.1
 ------------------------------