diff --git a/scraibe/email_sender.py b/scraibe/email_sender.py
index 2401f2e..0072ee8 100644
--- a/scraibe/email_sender.py
+++ b/scraibe/email_sender.py
@@ -496,13 +496,28 @@ def create_transcript_docx(text: str, filename: str):
         if current:
             content_lines.append(current)
 
-        # First visual line: include label if present
+        # First visual line: include label if present, ensuring total <= max_chars
         if content_lines:
-            first_line_text = (label_text + " " if label_text else "") + content_lines[0]
+            first_content = content_lines.pop(0)
+            if label_text:
+                prefix = label_text + " "
+                # If too long, trim first_content at word boundary
+                if len(prefix) + len(first_content) > max_chars:
+                    allowed = max_chars - len(prefix)
+                    if allowed < 1:
+                        allowed = 1
+                    # Truncate at word boundary
+                    candidate = first_content[:allowed]
+                    last_space = candidate.rfind(" ")
+                    if last_space > 0:
+                        candidate = candidate[:last_space]
+                    first_content = candidate
+                first_line_text = prefix + first_content
+            else:
+                first_line_text = first_content
+
             line_number += 1
             _add_transcript_paragraph(doc, first_line_text, line_number=line_number)
-            # Remove remaining content lines' leading content (already done) from first line
-            content_lines = content_lines[1:]
 
         # Subsequent visual lines: no label, just content
         for cl in content_lines: