diff --git a/pkgs/gui-pkgs/gui-lib/mred/private/wx/cocoa/button.rkt b/pkgs/gui-pkgs/gui-lib/mred/private/wx/cocoa/button.rkt
index 288413b5a2..1983c9d568 100644
--- a/pkgs/gui-pkgs/gui-lib/mred/private/wx/cocoa/button.rkt
+++ b/pkgs/gui-pkgs/gui-lib/mred/private/wx/cocoa/button.rkt
@@ -53,7 +53,8 @@
       (when button-type
         (tellv cocoa setButtonType: #:type _int button-type))
       (unless button-type
-        (tellv cocoa setBezelStyle: #:type _int (if (not (string? label))
+        (tellv cocoa setBezelStyle: #:type _int (if (or (not (string? label))
+                                                        (regexp-match? #rx"\n" label))
                                                     NSRegularSquareBezelStyle
                                                     NSRoundedBezelStyle)))
       (cond
diff --git a/pkgs/gui-pkgs/gui-lib/mred/private/wx/win32/button.rkt b/pkgs/gui-pkgs/gui-lib/mred/private/wx/win32/button.rkt
index ba9e04b801..643340541c 100644
--- a/pkgs/gui-pkgs/gui-lib/mred/private/wx/win32/button.rkt
+++ b/pkgs/gui-pkgs/gui-lib/mred/private/wx/win32/button.rkt
@@ -55,7 +55,7 @@
 							    [(right) BS_RIGHT]
 							    [(top) BS_TOP]
 							    [(bottom) BS_BOTTOM])
-                                                          0))
+                                                          BS_MULTILINE))
                                          0 0 0 0
                                          (send parent get-content-hwnd)
                                          #f
diff --git a/pkgs/gui-pkgs/gui-lib/mred/private/wx/win32/window.rkt b/pkgs/gui-pkgs/gui-lib/mred/private/wx/win32/window.rkt
index 12949402bb..2d0079575f 100644
--- a/pkgs/gui-pkgs/gui-lib/mred/private/wx/win32/window.rkt
+++ b/pkgs/gui-pkgs/gui-lib/mred/private/wx/win32/window.rkt
@@ -383,7 +383,10 @@
                                    (values (combine-w w1 w2) (combine-h h1 h2)
                                            (combine-h d1 d1) (combine-h a1 a2)))]
                                 [else
-                                 (send measure-dc get-text-extent label #f #t)]))]
+                                 (define strs (regexp-split #rx"\n" label))
+                                 (for/fold ([w 0][h 0][d 0] [a 0]) ([str (in-list strs)])
+                                   (define-values (tw th d a) (send measure-dc get-text-extent label #f #t))
+                                   (values (max w tw) (+ h th) 0 0))]))]
                   [(->int) (lambda (v) (inexact->exact (ceiling v)))])
        (resize (->int (* scale-h (max (+ w dw) min-w)))
                (->int (* scale-w (max (+ h dh) min-h)))))))