I did something like this once for a client a very long time ago, so the code
isn't wonderful but it did the trick...

When they clicked a particular formfield, I had a small dialog box appear to
enter the text and wrote the following code behind the OK button. I had
already figured out what number of characters normally fit into the area so
if the text exceeded this limit, I reduced it's size.
"FrmBriefDescriptionOfLand" is the name of the userform, and
"txtBriefDescriptionOfLand" is the text control in the userform.

If FrmBriefDescriptionOfLand.TxtBriefDescriptionOfLand.TextLength > 281 Then
With Selection.Paragraphs(1).Range.Font
      .Size = 8
   End With
End If

Hope this helps,

JillE

Hi:

After you have written the text into the textbox, you could try:

Sub AA()
   With ActiveDocument.Shapes(X).TextFrame
       Do
           .TextRange.Font.Shrink
       Loop While .Overflowing
   End With
End Sub

- where shapes(X) is your textbox.

If you give the textbox a name:

ActiveDocument.Shapes(X).Name="Fred"

- then you can say:

Sub AA()
   With ActiveDocument.Shapes("Fred").TextFrame
       Do
           .TextRange.Font.Shrink
       Loop While .Overflowing
   End With
End Sub