diff --git a/src/graphics/text.c b/src/graphics/text.c
index ea5e3e10de..e602813c86 100644
--- a/src/graphics/text.c
+++ b/src/graphics/text.c
@@ -419,8 +419,9 @@ int text_draw_multiline(const uint8_t *str, int x_offset, int y_offset, int box_
     return y - y_offset;
 }
 
-int text_measure_multiline(const uint8_t *str, int box_width, font_t font)
+int text_measure_multiline(const uint8_t *str, int box_width, font_t font, int *largest_width)
 {
+    *largest_width = 0;
     int has_more_characters = 1;
     int guard = 0;
     int num_lines = 0;
@@ -429,7 +430,7 @@ int text_measure_multiline(const uint8_t *str, int box_width, font_t font)
             break;
         }
         int current_width = 0;
-        while (has_more_characters && current_width < box_width) {
+        while (has_more_characters) {
             int word_num_chars;
             int word_width = get_word_width(str, font, &word_num_chars);
             current_width += word_width;
@@ -437,6 +438,7 @@ int text_measure_multiline(const uint8_t *str, int box_width, font_t font)
                 if (current_width == 0) {
                     has_more_characters = 0;
                 }
+                break;
             } else {
                 str += word_num_chars;
                 if (!*str) {
@@ -447,6 +449,9 @@ int text_measure_multiline(const uint8_t *str, int box_width, font_t font)
                 }
             }
         }
+        if (current_width > *largest_width) {
+            *largest_width = current_width;
+        }
         num_lines += 1;
     }
     return num_lines;
diff --git a/src/graphics/text.h b/src/graphics/text.h
index 449a2ea012..503155f28d 100644
--- a/src/graphics/text.h
+++ b/src/graphics/text.h
@@ -36,6 +36,6 @@ int text_draw_multiline(const uint8_t *str, int x_offset, int y_offset, int box_
 /**
  * @return Number of lines required to draw the text
  */
-int text_measure_multiline(const uint8_t *str, int box_width, font_t font);
+int text_measure_multiline(const uint8_t *str, int box_width, font_t font, int *largest_width);
 
 #endif // GRAPHICS_TEXT_H
diff --git a/src/graphics/tooltip.c b/src/graphics/tooltip.c
index 567c155e2f..516c4db5d4 100644
--- a/src/graphics/tooltip.c
+++ b/src/graphics/tooltip.c
@@ -132,12 +132,14 @@ static void draw_button_tooltip(tooltip_context *c)
     const uint8_t *text = get_tooltip_text(c);
 
     int width = 200;
-    int lines = text_measure_multiline(text, width - 5, FONT_SMALL_PLAIN);
+    int largest_width;
+    int lines = text_measure_multiline(text, width - 16, FONT_SMALL_PLAIN, &largest_width);
     if (lines > 2) {
         width = 300;
-        lines = text_measure_multiline(text, width - 5, FONT_SMALL_PLAIN);
+        lines = text_measure_multiline(text, width - 16, FONT_SMALL_PLAIN, &largest_width);
     }
     int height = 16 * lines + 10;
+    width = largest_width + 16;
 
     int x, y;
     if (c->mouse_x < screen_dialog_offset_x() + width + 100) {
@@ -191,19 +193,21 @@ static void draw_button_tooltip(tooltip_context *c)
 
     graphics_draw_rect(x, y, width, height, COLOR_BLACK);
     graphics_fill_rect(x + 1, y + 1, width - 2, height - 2, COLOR_WHITE);
-    text_draw_multiline(text, x + 5, y + 7, width - 5, FONT_SMALL_PLAIN, COLOR_TOOLTIP);
+    text_draw_multiline(text, x + 8, y + 8, width - 15, FONT_SMALL_PLAIN, COLOR_TOOLTIP);
 }
 
 static void draw_overlay_tooltip(tooltip_context *c)
 {
     const uint8_t *text = get_tooltip_text(c);
     int width = 200;
-    int lines = text_measure_multiline(text, width - 5, FONT_SMALL_PLAIN);
+    int largest_width;
+    int lines = text_measure_multiline(text, width - 16, FONT_SMALL_PLAIN, &largest_width);
     if (lines > 2) {
         width = 300;
-        lines = text_measure_multiline(text, width - 5, FONT_SMALL_PLAIN);
+        lines = text_measure_multiline(text, width - 16, FONT_SMALL_PLAIN, &largest_width);
     }
     int height = 16 * lines + 10;
+    width = largest_width + 16;
 
     int x, y;
     if (c->mouse_x < width + 20) {
@@ -223,7 +227,7 @@ static void draw_overlay_tooltip(tooltip_context *c)
 
     graphics_draw_rect(x, y, width, height, COLOR_BLACK);
     graphics_fill_rect(x + 1, y + 1, width - 2, height - 2, COLOR_WHITE);
-    text_draw_multiline(text, x + 5, y + 7, width - 5, FONT_SMALL_PLAIN, COLOR_TOOLTIP);
+    text_draw_multiline(text, x + 8, y + 8, width - 15, FONT_SMALL_PLAIN, COLOR_TOOLTIP);
 }
 
 static void draw_senate_tooltip(tooltip_context *c)