diff --git a/source/blender/editors/interface/regions/interface_region_tooltip.cc b/source/blender/editors/interface/regions/interface_region_tooltip.cc
index bbdf5ad5982..abc2914daea 100644
--- a/source/blender/editors/interface/regions/interface_region_tooltip.cc
+++ b/source/blender/editors/interface/regions/interface_region_tooltip.cc
@@ -1897,7 +1897,7 @@ static void ui_tooltip_from_vfont(const VFont &font, uiTooltipData &data)
   float color[4];
   const uiWidgetColors *theme = ui_tooltip_get_theme();
   rgba_uchar_to_float(color, theme->text);
-  ImBuf *ibuf = IMB_font_preview(filepath_abs, 200 * UI_SCALE_FAC, color);
+  ImBuf *ibuf = IMB_font_preview(filepath_abs, 256 * UI_SCALE_FAC, color, "ABCDabefg&0123");
   if (ibuf) {
     uiTooltipImage image_data;
     image_data.width = ibuf->x;
diff --git a/source/blender/editors/space_file/file_draw.cc b/source/blender/editors/space_file/file_draw.cc
index d52cf7f6ffb..42532d1172b 100644
--- a/source/blender/editors/space_file/file_draw.cc
+++ b/source/blender/editors/space_file/file_draw.cc
@@ -279,6 +279,16 @@ static void file_draw_tooltip_custom_func(bContext & /*C*/,
         }
       }
     }
+    else if (file->typeflag & FILE_TYPE_FTFONT) {
+      float color[4];
+      bTheme *btheme = UI_GetTheme();
+      rgba_uchar_to_float(color, btheme->tui.wcol_tooltip.text);
+      thumb = IMB_font_preview(full_path,
+                               512 * UI_SCALE_FAC,
+                               color,
+                               TIP_("The five boxing wizards jump quickly! 0123456789"));
+      free_imbuf = true;
+    }
 
     char date_str[FILELIST_DIRENTRY_DATE_LEN], time_str[FILELIST_DIRENTRY_TIME_LEN];
     bool is_today, is_yesterday;
@@ -321,7 +331,20 @@ static void file_draw_tooltip_custom_func(bContext & /*C*/,
     }
   }
 
-  if (thumb && params->display != FILE_IMGDISPLAY) {
+  if (thumb && file->typeflag & FILE_TYPE_FTFONT) {
+    const float scale = (512.0f * UI_SCALE_FAC) / float(std::max(thumb->x, thumb->y));
+    uiTooltipImage image_data;
+    image_data.ibuf = thumb;
+    image_data.width = short(float(thumb->x) * scale);
+    image_data.height = short(float(thumb->y) * scale);
+    image_data.background = uiTooltipImageBackground::None;
+    image_data.premultiplied = false;
+    image_data.text_color = true;
+    image_data.border = false;
+    UI_tooltip_text_field_add(tip, {}, {}, UI_TIP_STYLE_SPACER, UI_TIP_LC_NORMAL);
+    UI_tooltip_image_field_add(tip, image_data);
+  }
+  else if (thumb && params->display != FILE_IMGDISPLAY) {
     UI_tooltip_text_field_add(tip, {}, {}, UI_TIP_STYLE_SPACER, UI_TIP_LC_NORMAL);
     UI_tooltip_text_field_add(tip, {}, {}, UI_TIP_STYLE_SPACER, UI_TIP_LC_NORMAL);
 
diff --git a/source/blender/imbuf/IMB_thumbs.hh b/source/blender/imbuf/IMB_thumbs.hh
index 3962b564035..a43ee11a19f 100644
--- a/source/blender/imbuf/IMB_thumbs.hh
+++ b/source/blender/imbuf/IMB_thumbs.hh
@@ -93,7 +93,10 @@ ImBuf *IMB_thumb_load_blend(const char *blen_path, const char *blen_group, const
 ImBuf *IMB_thumb_load_font(const char *filepath, unsigned int x, unsigned int y);
 bool IMB_thumb_load_font_get_hash(char *r_hash);
 
-ImBuf *IMB_font_preview(const char *filepath, unsigned int width, const float color[4]);
+ImBuf *IMB_font_preview(const char *filepath,
+                        unsigned int width,
+                        const float color[4],
+                        const char *sample_text = nullptr);
 
 /* Threading */
 
diff --git a/source/blender/imbuf/intern/thumbs_font.cc b/source/blender/imbuf/intern/thumbs_font.cc
index 016af84c9b7..85d5579155e 100644
--- a/source/blender/imbuf/intern/thumbs_font.cc
+++ b/source/blender/imbuf/intern/thumbs_font.cc
@@ -45,27 +45,30 @@ bool IMB_thumb_load_font_get_hash(char *r_hash)
   return true;
 }
 
-ImBuf *IMB_font_preview(const char *filepath, uint width, const float color[4])
+ImBuf *IMB_font_preview(const char *filepath,
+                        uint width,
+                        const float color[4],
+                        const char *sample_text)
 {
   int font_id = (filepath[0] != '<') ? BLF_load(filepath) : 0;
   if (font_id == -1) {
     return nullptr;
   }
-  const char sample[] = "ABCDEFGH\nabcdefg123";
+  const char default_sample[] = "ABCDabefg&0123";
+  const char *sample = sample_text ? sample_text : default_sample;
 
   BLF_buffer_col(font_id, color);
 
   BLF_size(font_id, 50.0f);
-  BLF_enable(font_id, BLF_WORD_WRAP);
   float name_w;
   float name_h;
-  BLF_width_and_height(font_id, sample, sizeof(sample), &name_w, &name_h);
-  float scale = float(width) / name_w;
+  BLF_width_and_height(font_id, sample, strlen(sample), &name_w, &name_h);
+  const float scale = float(width) / name_w * 0.98f;
   BLF_size(font_id, scale * 50.0f);
   name_w *= scale;
   name_h *= scale;
 
-  int height = int(name_h * 1.3f);
+  const int height = int(name_h * 1.8f);
   ImBuf *ibuf = IMB_allocImBuf(width, height, 32, IB_byte_data);
   /* fill with white and zero alpha */
   const float col[4] = {1.0f, 1.0f, 1.0f, 0.0f};
@@ -73,7 +76,7 @@ ImBuf *IMB_font_preview(const char *filepath, uint width, const float color[4])
 
   BLF_buffer(font_id, ibuf->float_buffer.data, ibuf->byte_buffer.data, width, height, nullptr);
 
-  BLF_position(font_id, 0.0f, name_h * 0.8f, 0.0f);
+  BLF_position(font_id, 0.0f, height * 0.3f, 0.0f);
   BLF_draw_buffer(font_id, sample, 1024);
 
   BLF_buffer(font_id, nullptr, nullptr, 0, 0, nullptr);