While posting a cry for help, I thought of and created a solution. Figured I would post it anyways since it works flawlessly. Maybe you know a better way.
Well I created an upload script and before the looping and swifting through data I wanted to ensure the filesize was legit before making the server work.
Everytime I grabbed the Filesize by getting the Request.TotalBytes, I would get http bad requests after a few attempts to upload a huge file to test the validation. I tried everything to get rid of the 500 errors but I had no luck.
The problem is the server is posting data over and nothing is catching it. When the file size was invalid I never read the bytes passed over. So what did I do? I read it anyways.
Dim FileSize : FileSize = Request.TotalBytes
Select Case (IsValidSize(CLng(FileSize)))
Case True: '=== More Validation ===
Case Else: SetErrorMessage()
End Select
Select Case (IsEmpty(m_ErrorMessage))
Case True: UploadFile(Request.BinaryRead(FileSize))
Case Else: Dim PlaceHolder : PlaceHolder = Request.BinaryRead(FileSize) : PlaceHolder = Null
SetIsSaved = False
End Select
Reading it and disposing of it clears all those bad requests away. Yay!
File reads are instantaneous and now the script rejects over sized files immediately rather then reading the file for several seconds then rejecting.