diff --git a/Tests/test_imagetext.py b/Tests/test_imagetext.py
index 699c4cba544..e55299469c2 100644
--- a/Tests/test_imagetext.py
+++ b/Tests/test_imagetext.py
@@ -170,6 +170,16 @@ def test_wrap_height() -> None:
     assert text.text == "Text does\nnot fit"
 
 
+def test_wrap_height_blank_line(layout_engine: ImageFont.Layout) -> None:
+    font = ImageFont.truetype(FONT_PATH, 10, layout_engine=layout_engine)
+    text = ImageText.Text("A\n\nB", font)
+
+    wrapped = text.wrap(100, 10)
+    assert wrapped is not None
+    assert wrapped.text == "\nB"
+    assert text.text == "A"
+
+
 def test_wrap_scaling_unsupported() -> None:
     font = ImageFont.load_default_imagefont()
     text = ImageText.Text("Hello World!", font)
@@ -227,6 +237,9 @@ def test_wrap_grow() -> None:
     with pytest.raises(ValueError, match="Text could not be scaled"):
         text.wrap(50, 10, "grow")
 
+    text.wrap(50, 30, "grow")
+    assert text.get_bbox()[3] <= 30
+
     text = ImageText.Text("Hello World!")
     assert text.wrap(50, 50, ("grow", 18)) is None
     assert isinstance(text.font, ImageFont.FreeTypeFont)
diff --git a/src/PIL/ImageText.py b/src/PIL/ImageText.py
index 10297d3f282..385491771ce 100644
--- a/src/PIL/ImageText.py
+++ b/src/PIL/ImageText.py
@@ -50,11 +50,15 @@ def __init__(
             if newlines:
                 if not self.add_line(line):
                     break
+                newlines_all_fit = True
                 for i, line in enumerate(newlines):
                     if i != 0 and not self.add_line(emptystring):
+                        newlines_all_fit = False
                         break
                     self.position += len(line)
                     word = word[len(line) :]
+                if not newlines_all_fit:
+                    break
                 line = emptystring
 
             new_line = line + word
@@ -85,7 +89,7 @@ def __init__(
     def add_line(self, line: AnyStr) -> bool:
         lines = self.lines + [line]
         if self.height is not None:
-            last_line_y = self.text._split(lines=lines)[-1].y
+            last_line_y = self.text._split(lines=lines, font=self.font)[-1].y
             last_line_height = self.text._get_bbox(line, self.font)[3]
             if last_line_y + last_line_height > self.height:
                 return False
@@ -331,6 +335,7 @@ def _split(
         anchor: str | None = None,
         align: str = "left",
         lines: list[str] | list[bytes] | None = None,
+        font: ImageFont.BaseImageFont | None = None,
     ) -> list[_Line]:
         if anchor is None:
             anchor = "lt" if self.direction == "ttb" else "la"
@@ -351,9 +356,11 @@ def _split(
             msg = "anchor not supported for multiline text"
             raise ValueError(msg)
 
+        if font is None:
+            font = self.font
         fontmode = self._get_fontmode()
         line_spacing = (
-            self.font.getbbox(
+            font.getbbox(
                 "A",
                 fontmode,
                 None,
@@ -376,7 +383,7 @@ def _split(
             widths = []
             max_width: float = 0
             for line in lines:
-                line_width = self.font.getlength(
+                line_width = font.getlength(
                     line, fontmode, self.direction, self.features, self.language
                 )
                 widths.append(line_width)
@@ -420,7 +427,7 @@ def _split(
                             left -= max_width
 
                         word_widths = [
-                            self.font.getlength(
+                            font.getlength(
                                 word,
                                 fontmode,
                                 self.direction,