SendKeys to FileDialog

I feel like I am 3/4 of the way to my objective. I've created VBA that will populate an automated e-mail with attachments, based on the name of a folder the user previously selected.

It goes like this:

'folderName is identified earlier
Dim files As FileDialog
Dim vrtSelectedItem As Variant
Dim list As String, wbName As String, atmpt As Long

wbName = Left(ThisWorkbook.Path, InStrRev(ThisWorkbook.Path, "/")) & _
         "Registry/Joining Instructions/" & folderName & "/"

Do
   Set files = Application.FileDialog(msoFileDialogFilePicker)
   cnt = 0
   atmpt = atmpt + 1
        
   With files
       .InitialFileName = wbName

       Application.SendKeys "+{TAB}", True
       Application.SendKeys "+{TAB}", True
       Application.SendKeys "^a", True
       Application.SendKeys "~", True
                    
       If .Show = -1 Then
            'Code continues...

The reason why I don't permanently set attachment names and simply attach them to every e-mail is because these attachments are dynamic and change with certain environments. Another thing I should mention is this workbook is located on SharePoint, so FileSystemObject is out of the question. Thus, I have the FileDialog appear, locate the specific folder that was previously identified, and I have it select all files.

My goal: is to have this fully automatic (mind you, ugly to the eye as it flickers for less than a few seconds).

My issue: is that this does not work on the first try, ever. On the first atmpt, the FileDialog opens but does not register the SendKeys. Every subsequent, uninterrupted attempt (even re-calling the subroutine) opens the FileDialog, locates the folder, selects all attachments, and closes as expected.

My question: what is making the very first instance of FileDialog different from any subsequent instance? I've perfected my SendKeys for all subsequent openings, but if I could just code it for the first instance, anything more won't be necessary.

Any help is appreciated! Thanks, Joey

If you use the VBA-FileTools library, you can avoid using FileDialog and SendKeys. By using GetLocalPath, you get the traditional format for the path. And using GetFiles from the same library, you can even get all files inside a subfolder relative to your workbook like this:

Sub DemoGetLocalPath()

    Dim SubFolderName As String
    SubFolderName = "Subfolder"
    
    Dim LocalFolderPath As String
    LocalFolderPath = GetLocalPath(ThisWorkbook.Path)
          
    Dim MyFiles As Collection
    Set MyFiles = GetFiles(LocalFolderPath & "\" & SubFolderName)
          
    Dim FilePath As Variant
    For Each FilePath In MyFiles
        Debug.Print FilePath
    Next

End Sub