diff --git a/kitty/cocoa_window.h b/kitty/cocoa_window.h
index 375f3fa89..3942f9e82 100644
--- a/kitty/cocoa_window.h
+++ b/kitty/cocoa_window.h
@@ -64,6 +64,7 @@ void cocoa_update_menu_bar_title(PyObject*);
 size_t cocoa_get_workspace_ids(void *w, size_t *workspace_ids, size_t array_sz);
 monotonic_t cocoa_cursor_blink_interval(void);
 bool cocoa_render_line_of_text(const char *text, const color_type fg, const color_type bg, uint8_t *rgba_output, const size_t width, const size_t height);
+size_t cocoa_text_width_for_single_line(const char *text, const size_t height);
 extern uint8_t* render_single_ascii_char_as_mask(const char ch, size_t *result_width, size_t *result_height);
 void get_cocoa_key_equivalent(uint32_t, int, char *key, size_t key_sz, int*);
 void set_cocoa_pending_action(CocoaPendingAction action, const char*);
diff --git a/kitty/core_text.m b/kitty/core_text.m
index c988a0c0e..d8fef7e29 100644
--- a/kitty/core_text.m
+++ b/kitty/core_text.m
@@ -974,6 +974,21 @@ cocoa_render_line_of_text(const char *text, const color_type fg, const color_typ
     return true;
 }
 
+size_t
+cocoa_text_width_for_single_line(const char *text, const size_t height) {
+    if (!text || !text[0]) return 0;
+    if (!ensure_ui_font(height)) return 0;
+    NSAttributedString *str = [[NSAttributedString alloc] initWithString:@(text) attributes:@{(NSString *)kCTFontAttributeName: (__bridge id)system_ui_font}];
+    if (!str) return 0;
+    CTLineRef line = CTLineCreateWithAttributedString((CFAttributedStringRef)str);
+    [str release];
+    if (!line) return 0;
+    CGFloat ascent, descent, leading;
+    double width = CTLineGetTypographicBounds(line, &ascent, &descent, &leading);
+    CFRelease(line);
+    return (size_t)ceil(width);
+}
+
 uint8_t*
 render_single_ascii_char_as_mask(const char ch, size_t *result_width, size_t *result_height) {
     if (!ensure_ui_font(*result_height)) { PyErr_SetString(PyExc_RuntimeError, "failed to create UI font"); return NULL; }
diff --git a/kitty/fast_data_types.pyi b/kitty/fast_data_types.pyi
index 73d6feb66..05f65ffe9 100644
--- a/kitty/fast_data_types.pyi
+++ b/kitty/fast_data_types.pyi
@@ -1846,7 +1846,7 @@ def start_drag_with_data(
     operations: int = GLFW_DRAG_OPERATION_MOVE
 ) -> None: ...
 def change_drag_thumbnail(os_window_id: int, idx: int = -1) -> None: ...
-def draw_single_line_of_text(os_window_id: int, text: str, fg: int, bg: int, width: int, padding_y: int = 2) -> bytes: ...
+def draw_single_line_of_text(os_window_id: int, text: str, fg: int, bg: int, width: int, padding_y: int = 2, max_width: bool = False) -> tuple[bytes, int]: ...
 def set_tab_being_dragged(tab_id: int = 0, drag_started: bool = False, x: float = 0, y: float = 0) -> None: ...
 def get_tab_being_dragged() -> tuple[int, bool, float, float]: ...
 def set_window_being_dragged(window_id: int = 0, drag_started: bool = False, x: float = 0.0, y: float = 0.0) -> None: ...
diff --git a/kitty/freetype_render_ui_text.c b/kitty/freetype_render_ui_text.c
index bed467ddf..d14d0eec0 100644
--- a/kitty/freetype_render_ui_text.c
+++ b/kitty/freetype_render_ui_text.c
@@ -483,6 +483,77 @@ end:
     return ok;
 }
 
+size_t
+freetype_text_width_for_single_line(FreeTypeRenderCtx ctx_, const char *text, unsigned sz_px) {
+    RenderCtx *ctx = (RenderCtx*)ctx_;
+    if (!ctx->created) return 0;
+    bool has_text = text && text[0];
+    if (!has_text) return 0;
+    hb_buffer_clear_contents(hb_buffer);
+    if (!hb_buffer_pre_allocate(hb_buffer, 512)) { PyErr_NoMemory(); return 0; }
+
+    size_t text_len = strlen(text);
+    char_type *unicode = calloc(text_len + 1, sizeof(char_type));
+    if (!unicode) { PyErr_NoMemory(); return 0; }
+    text_len = decode_utf8_string(text, text_len, unicode);
+    set_pixel_size(ctx, &main_face, sz_px, true);
+    // Use a very large output_width so nothing is truncated
+    RenderState rs = {
+        .current_face = &main_face, .fg = 0, .bg = 0, .horizontally_center = false,
+        .output_width = SIZE_MAX, .output_height = 0, .stride = 0,
+        .output = NULL, .x = 0, .y = 0, .sz_px = sz_px
+    };
+
+    for (size_t i = 0; i < text_len; i++) {
+        bool add_to_current_buffer = false;
+        char_type codep = unicode[i];
+        char_type next_codep = unicode[i + 1];
+        Face *fallback_font = NULL;
+        if (char_props_for(codep).is_combining_char) {
+            add_to_current_buffer = true;
+        } else if (glyph_id_for_codepoint(&main_face, codep) > 0) {
+            add_to_current_buffer = rs.current_face == &main_face;
+            if (!add_to_current_buffer) fallback_font = &main_face;
+        } else {
+            if (glyph_id_for_codepoint(rs.current_face, codep) > 0) fallback_font = rs.current_face;
+            else fallback_font = find_fallback_font_for(ctx, codep, next_codep);
+            add_to_current_buffer = !fallback_font || rs.current_face == fallback_font;
+        }
+        if (!add_to_current_buffer) {
+            if (rs.pending_in_buffer) {
+                // Shape the current run and accumulate width
+                hb_buffer_guess_segment_properties(hb_buffer);
+                set_pixel_size(ctx, rs.current_face, sz_px, false);
+                hb_shape(rs.current_face->hb, hb_buffer, NULL, 0);
+                unsigned int len = hb_buffer_get_length(hb_buffer);
+                hb_glyph_position_t *positions = hb_buffer_get_glyph_positions(hb_buffer, NULL);
+                for (unsigned int j = 0; j < len; j++) {
+                    rs.x += (float)positions[j].x_offset / 64.0f + (float)positions[j].x_advance / 64.0f;
+                }
+                rs.pending_in_buffer = 0;
+                hb_buffer_clear_contents(hb_buffer);
+            }
+            if (fallback_font) rs.current_face = fallback_font;
+        }
+        hb_buffer_add_utf32(hb_buffer, &codep, 1, 0, 1);
+        rs.pending_in_buffer += 1;
+    }
+    if (rs.pending_in_buffer) {
+        hb_buffer_guess_segment_properties(hb_buffer);
+        set_pixel_size(ctx, rs.current_face, sz_px, false);
+        hb_shape(rs.current_face->hb, hb_buffer, NULL, 0);
+        unsigned int len = hb_buffer_get_length(hb_buffer);
+        hb_glyph_position_t *positions = hb_buffer_get_glyph_positions(hb_buffer, NULL);
+        for (unsigned int j = 0; j < len; j++) {
+            rs.x += (float)positions[j].x_offset / 64.0f + (float)positions[j].x_advance / 64.0f;
+        }
+        hb_buffer_clear_contents(hb_buffer);
+    }
+
+    free(unicode);
+    return (size_t)ceilf(rs.x);
+}
+
 static uint8_t*
 render_single_char_bitmap(const FT_Bitmap *bm, size_t *result_width, size_t *result_height) {
     *result_width = bm->width; *result_height = bm->rows;
diff --git a/kitty/freetype_render_ui_text.h b/kitty/freetype_render_ui_text.h
index 5c7d4366b..5b1d59502 100644
--- a/kitty/freetype_render_ui_text.h
+++ b/kitty/freetype_render_ui_text.h
@@ -14,6 +14,7 @@ typedef struct {bool created;} *FreeTypeRenderCtx;
 FreeTypeRenderCtx create_freetype_render_context(const char *family, bool bold, bool italic);
 void set_main_face_family(FreeTypeRenderCtx ctx, const char *family, bool bold, bool italic);
 bool render_single_line(FreeTypeRenderCtx ctx, const char *text, unsigned sz_px, uint32_t fg, uint32_t bg, uint8_t *output_buf, size_t width, size_t height, float x_offset, float y_offset, size_t right_margin, bool horizontally_center_runs);
+size_t freetype_text_width_for_single_line(FreeTypeRenderCtx ctx, const char *text, unsigned sz_px);
 uint8_t* render_single_ascii_char_as_mask(FreeTypeRenderCtx ctx_, const char ch, size_t *result_width, size_t *result_height);
 void release_freetype_render_context(FreeTypeRenderCtx ctx);
 
diff --git a/kitty/glfw.c b/kitty/glfw.c
index 15f35d94e..7cc51d264 100644
--- a/kitty/glfw.c
+++ b/kitty/glfw.c
@@ -1160,6 +1160,13 @@ draw_window_title(double font_sz_pts UNUSED, double ydpi UNUSED, const char *tex
     return cocoa_render_line_of_text(buf, fg, bg, output_buf, width, height);
 }
 
+size_t
+text_width_for_single_line(double font_sz_pts UNUSED, double ydpi UNUSED, const char *text, size_t height) {
+    static char buf[2048];
+    strip_csi_(text, buf, arraysz(buf));
+    return cocoa_text_width_for_single_line(buf, height);
+}
+
 
 uint8_t*
 draw_single_ascii_char(const char ch, size_t *result_width, size_t *result_height) {
@@ -1218,6 +1225,17 @@ draw_window_title(double font_sz_pts, double ydpi, const char *text, color_type
     return ok;
 }
 
+size_t
+text_width_for_single_line(double font_sz_pts, double ydpi, const char *text, size_t height) {
+    FreeTypeRenderCtx ctx;
+    if (!(ctx = freetype_render_ctx(false))) return 0;
+    static char buf[2048];
+    strip_csi_(text, buf, arraysz(buf));
+    unsigned px_sz = (unsigned)(font_sz_pts * ydpi / 72.);
+    px_sz = MIN(px_sz, 3 * height / 4);
+    return freetype_text_width_for_single_line(ctx, buf, px_sz);
+}
+
 uint8_t*
 draw_single_ascii_char(const char ch, size_t *result_width, size_t *result_height) {
     FreeTypeRenderCtx ctx;
@@ -3081,8 +3099,8 @@ draw_single_line_of_text(PyObject *self UNUSED, PyObject *args) {
     unsigned long long os_window_id;
     const char *text;
     unsigned int fg, bg;
-    int width, padding_y = 2;
-    if (!PyArg_ParseTuple(args, "KsIIi|i", &os_window_id, &text, &fg, &bg, &width, &padding_y)) return NULL;
+    int width, padding_y = 2, max_width = 0;
+    if (!PyArg_ParseTuple(args, "KsIIi|ip", &os_window_id, &text, &fg, &bg, &width, &padding_y, &max_width)) return NULL;
     OSWindow *w = os_window_for_id(os_window_id);
     if (!w || !w->fonts_data) {
         PyErr_SetString(PyExc_KeyError, "OS Window with specified id does not exist or has no fonts data");
@@ -3091,13 +3109,17 @@ draw_single_line_of_text(PyObject *self UNUSED, PyObject *args) {
     double font_sz_pts = w->fonts_data->font_sz_in_pts;
     double ydpi = w->fonts_data->logical_dpi_y;
     size_t height = (size_t)w->fonts_data->fcm.cell_height + padding_y;
+    if (max_width) {
+        size_t text_w = text_width_for_single_line(font_sz_pts, ydpi, text, height);
+        if (text_w > 0 && (int)text_w < width) width = (int)text_w;
+    }
     size_t buf_sz = (size_t)width * height * 4;
     RAII_PyObject(ans, PyBytes_FromStringAndSize(NULL, buf_sz)); if (!ans) return NULL;
     if (!draw_window_title(font_sz_pts, ydpi, text, fg, bg, (uint8_t*)PyBytes_AS_STRING(ans), width, height)) {
         if (!PyErr_Occurred()) PyErr_SetString(PyExc_RuntimeError, "Failed to render text");
         return NULL;
     }
-    return Py_NewRef(ans);
+    return Py_BuildValue("Oi", ans, width);
 }
 
 static bool
diff --git a/kitty/state.h b/kitty/state.h
index fb0a513d0..79d18de09 100644
--- a/kitty/state.h
+++ b/kitty/state.h
@@ -573,6 +573,7 @@ void dispatch_pending_clicks(id_type, void*);
 void send_pending_click_to_window(Window*, int);
 void get_platform_dependent_config_values(void *glfw_window);
 bool draw_window_title(double, double, const char *text, color_type fg, color_type bg, uint8_t *output_buf, size_t width, size_t height);
+size_t text_width_for_single_line(double font_sz_pts, double ydpi, const char *text, size_t height);
 uint8_t* draw_single_ascii_char(const char ch, size_t *result_width, size_t *result_height);
 bool is_os_window_fullscreen(OSWindow *);
 void update_ime_focus(OSWindow* osw, bool focused);
diff --git a/kitty/tabs.py b/kitty/tabs.py
index f30d245ab..a1026681f 100644
--- a/kitty/tabs.py
+++ b/kitty/tabs.py
@@ -1762,7 +1762,7 @@ class TabManager:  # {{{
                 else:
                     fg = color_as_int(opts.inactive_tab_foreground)
                     bg = color_as_int(opts.inactive_tab_background)
-                title_pixels = draw_single_line_of_text(self.os_window_id, title, 0xff000000 | fg, 0xff000000 | bg, width)
+                title_pixels, width = draw_single_line_of_text(self.os_window_id, title, 0xff000000 | fg, 0xff000000 | bg, width)
                 title_height = len(title_pixels) // (width * 4)
                 thumbnails = ((title_pixels, width, title_height), (title_pixels + pixels, width, title_height + height))
                 drag_data = {
@@ -1870,7 +1870,7 @@ class TabManager:  # {{{
         title = str(w.title or '')
         fg = color_as_int(opts.window_title_bar_active_foreground or opts.active_tab_foreground)
         bg = color_as_int(opts.window_title_bar_active_background or opts.active_tab_background)
-        title_pixels = draw_single_line_of_text(self.os_window_id, title, 0xff000000 | fg, 0xff000000 | bg, width)
+        title_pixels, width = draw_single_line_of_text(self.os_window_id, title, 0xff000000 | fg, 0xff000000 | bg, width)
         title_height = len(title_pixels) // (width * 4)
         thumbnails = ((title_pixels + pixels, width, title_height + height),)
         drag_data = {f'application/net.kovidgoyal.kitty-window-{os.getpid()}': str(window_id).encode()}
diff --git a/kitty/window.py b/kitty/window.py
index 0f08e0cd3..baaf1b88f 100644
--- a/kitty/window.py
+++ b/kitty/window.py
@@ -1321,7 +1321,7 @@ class Window:
         fg = color_as_int(self.screen.color_profile.default_fg)
         bg = color_as_int(self.screen.color_profile.default_bg)
         width = self.geometry.right - self.geometry.left
-        pixels = draw_single_line_of_text(self.os_window_id, url, 0xff000000 | fg, 0xff000000 | bg, width)
+        pixels, width = draw_single_line_of_text(self.os_window_id, url, 0xff000000 | fg, 0xff000000 | bg, width)
         height = len(pixels) // (width * 4)
         thumbnails = ((pixels, width, height),)
         drag_data = {'text/uri-list': (url + '\r\n').encode()}