The problem appears to be related to the presence of fields in your content. Try:
Code:
Sub Demo()
Application.ScreenUpdating = False
With ActiveDocument.Range
With .Find
.ClearFormatting
.Replacement.ClearFormatting
.Text = "^t"
.Forward = True
.Wrap = wdFindStop
End With
Do While .Find.Execute = True
.Start = .Paragraphs(1).Range.Start
If Len(.Text) - Len(Replace(.Text, vbTab, "")) > 1 Then .Characters.Last.Text = " "
.Collapse wdCollapseEnd
Loop
End With
Application.ScreenUpdating = True
End Sub