diff --git a/src/tuxpaint.c b/src/tuxpaint.c
index 4fbb52724..f6f7a9bf0 100644
--- a/src/tuxpaint.c
+++ b/src/tuxpaint.c
@@ -7948,7 +7948,7 @@ static SDL_Surface *do_render_button_label(const char *const label)
 
   if (button_w <= ORIGINAL_BUTTON_SIZE)
     myfont = small_font;
-  else if (button_w <= ORIGINAL_BUTTON_SIZE * 2)
+  else if (button_w <= ORIGINAL_BUTTON_SIZE * 3)
     myfont = medium_font;
   else
     myfont = large_font;
@@ -7957,6 +7957,7 @@ static SDL_Surface *do_render_button_label(const char *const label)
     myfont = locale_font;
   tmp_surf = render_text(myfont, upstr, black);
   free(upstr);
+
   surf = thumbnail(tmp_surf, min(button_w, tmp_surf->w), min(18 * button_scale + button_label_y_nudge, tmp_surf->h), 0);
   SDL_FreeSurface(tmp_surf);