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First the Situation: I'm trying to automate an image uploading utility which lives on the client side of some cloud based server/client software and which was not designed to be automated. I've got a 2012 R2 VM running with autologon enabled on a local account. The account with autologon enabled has a scheduled task set up to run at 4AM daily. This task merely runs my AutoIt script. Now the issue: If I remote into my VM and run the script manually, it runs perfectly. If I edit my scheduled task to run only a few minutes in the future, and then reboot the VM, it also works perfectly. If I leave it to run overnight, the script starts but never finishes. It seems to be getting hung up waiting for the first window to become active. I've tried many version of the script now with no luck. The latest version is below. #include <File.au3> Dim $un = "username" Dim $pw = "password" ; Login window Run("C:\Program Files (x86)\CSI Software\Spectrum NG\Spectrum NG Client\SNGImageUploader.exe") Dim $hLogin = WinWait("[CLASS:WindowsForms10.Window.8.app.0.2bf8098_r11_ad1]", "Version: ") SendKeepActive($hLogin) WinActivate($hLogin) Send($un & "{TAB}" & $pw & "{ENTER}") SendKeepActive("") ; Main window - 1/3 Dim $hMain = WinWaitActive("SNG Image Uploader") SendKeepActive($hMain) Send("{TAB}{ENTER}") SendKeepActive("") ; File browser window Dim $hBrowse = WinWaitActive("Browse For Folder") SendKeepActive($hBrowse) Send("{DOWN}{DOWN}{DOWN}{DOWN}{DOWN}{DOWN}{DOWN}{DOWN}{RIGHT}{DOWN}") Sleep(2000) ; Give the program moment to detect images in the directory Send("{ENTER}") SendKeepActive("") ; Main window - 2/3 SendKeepActive($hMain) WinWaitActive($hMain) Send("{TAB}{ENTER}") SendKeepActive("") ; Upload complete window Dim $hUpload = WinWaitActive("[CLASS:#32770]", "Upload complete. Please wait while servers process your request.") SendKeepActive($hUpload) Send("{ENTER}") SendKeepActive("") ; Import complete window Dim $hImport = WinWaitActive("[CLASS:#32770]", "Image import completed. Please check results in the Account Upload History screen.") SendKeepActive($hImport) Send("{ENTER}") SendKeepActive("") ; Main window - 3/3 WinWaitActive($hMain) WinClose($hMain) ; Cleanup FileDelete("C:\CRPics\*")