diff --git a/source/blender/blenfont/intern/blf_font.cc b/source/blender/blenfont/intern/blf_font.cc
index 5732fc0ece0..29507ee2bd9 100644
--- a/source/blender/blenfont/intern/blf_font.cc
+++ b/source/blender/blenfont/intern/blf_font.cc
@@ -1304,17 +1304,18 @@ static void blf_font_wrap_apply(FontBLF *font,
      * This is _only_ done when we know for sure the character is ascii (newline or a space).
      */
     pen_x_next = pen_x + advance_x;
-    if (UNLIKELY((int(mode) & int(BLFWrapMode::HardLimit)) && (pen_x_next >= wrap.wrap_width) &&
-                 (advance_x != 0)))
+
+    if (UNLIKELY((pen_x_next >= wrap.wrap_width) && (wrap.start != wrap.last[0]))) {
+      do_draw = true;
+    }
+    else if (UNLIKELY((int(mode) & int(BLFWrapMode::HardLimit)) &&
+                      (pen_x_next >= wrap.wrap_width) && (advance_x != 0)))
     {
       wrap.last[0] = i_curr;
       wrap.last[1] = i_curr;
       do_draw = true;
       clip_bytes = 0;
     }
-    else if (UNLIKELY((pen_x_next >= wrap.wrap_width) && (wrap.start != wrap.last[0]))) {
-      do_draw = true;
-    }
     else if (UNLIKELY(((i < str_len) && str[i]) == 0)) {
       /* Need check here for trailing newline, else we draw it. */
       wrap.last[0] = i + ((codepoint != '\n') ? 1 : 0);
diff --git a/source/blender/editors/interface/regions/interface_region_tooltip.cc b/source/blender/editors/interface/regions/interface_region_tooltip.cc
index bb4cfb8108a..4d4d938f850 100644
--- a/source/blender/editors/interface/regions/interface_region_tooltip.cc
+++ b/source/blender/editors/interface/regions/interface_region_tooltip.cc
@@ -214,8 +214,16 @@ static void ui_tooltip_region_draw_cb(const bContext * /*C*/, ARegion *region)
   color_blend_f3_f3(alert_color, main_color, 0.3f);
 
   /* Draw text. */
-  BLF_wordwrap(data->fstyle.uifont_id, data->wrap_width);
-  BLF_wordwrap(blf_mono_font, data->wrap_width);
+
+  /* Wrap most text typographically with hard width limit. */
+  BLF_wordwrap(data->fstyle.uifont_id,
+               data->wrap_width,
+               BLFWrapMode(int(BLFWrapMode::Typographical) | int(BLFWrapMode::HardLimit)));
+
+  /* Wrap paths with path-specific wrapping with hard width limit. */
+  BLF_wordwrap(blf_mono_font,
+               data->wrap_width,
+               BLFWrapMode(int(BLFWrapMode::Path) | int(BLFWrapMode::HardLimit)));
 
   bbox.xmin += 0.5f * pad_x; /* add padding to the text */
   bbox.ymax -= 0.5f * pad_y;
@@ -1300,8 +1308,12 @@ static ARegion *ui_tooltip_create_with_data(bContext *C,
   font_flag |= BLF_WORD_WRAP;
   BLF_enable(data->fstyle.uifont_id, font_flag);
   BLF_enable(blf_mono_font, font_flag);
-  BLF_wordwrap(data->fstyle.uifont_id, data->wrap_width);
-  BLF_wordwrap(blf_mono_font, data->wrap_width);
+  BLF_wordwrap(data->fstyle.uifont_id,
+               data->wrap_width,
+               BLFWrapMode(int(BLFWrapMode::Typographical) | int(BLFWrapMode::HardLimit)));
+  BLF_wordwrap(blf_mono_font,
+               data->wrap_width,
+               BLFWrapMode(int(BLFWrapMode::Path) | int(BLFWrapMode::HardLimit)));
 
   int i, fonth, fontw;
   for (i = 0, fontw = 0, fonth = 0; i < data->fields.size(); i++) {