SendKeys doesn't interact with popup window

[tjdickinson]

I've resorted to using SendKeys for the time being to create a PDF from my workbook using Acrobat (so the file has bookmarks). I've mapped out the key sequence:

Sub exportPDF()

Workbooks(ActiveWorkbook.Name).Activate
SendKeys "%y2", True
SendKeys "c", True
SendKeys "w", True

Application.Wait (Now() + TimeValue("00:00:10"))

SendKeys "{ENTER}", True

Application.Wait (Now() + TimeValue("00:00:03"))

SendKeys "{ENTER}", True

End Sub

Three things happen:

1. There is a long delay before opening the Create PDF window (which is done in the first two SendKeys actions); could the Application.Wait be interfering?
2. Nothing more happens when the Create PDF pop up opens. When I ran it with debug.print, all the keystrokes were recorded. So it's sending them, but they're not being registered by the pop up window.
3. NumLock always gets deactivated. No clue why.

I tried using Application.Wait (suggested here), Application.OnTime (suggested here), and adding a DoEvents sub (suggested here), but none of these have helped reliably. I've also tried longer wait times, but that didn't fix it.

The main issue is getting the Create PDF window to respond to the first "enter" key, and I imagine the issue will be the same when the save dialog opens. Any help is greatly appreciated. Thanks!