How to Fix Files No Longer Automatically Saving in Chrome-Save As Window Pops Up

I download a lot of attachments to my hard drive from my gmail account and a trend has developed.  Normally, to download, I would click on the download arrow on the attachment in gmail:

Click on the down-pointing arrow on the attachment in gmail to download

It then automatically downloads and the file can be seen in the bar at the bottom of Chrome:

Download bar at the bottom of Chrome

After some time, Chrome stopped automatically downloading files and whenever I click on the download arrow the “Save As” window pops up:

“Save As” window pops up now when I click on the download link

It turns out that the issue is a combination of things.  The file I am downloading is from my scanner, which names all attachments, Image.pdf.  OS 10.9 Mavericks (and 10.8 and earlier before it) would automatically append a (1), (2), (3)…. (100) to the file if there was already a file in the default downloads directory named Image.pdf or Image (1).pdf, Image (2).pdf… Image (100).pdf.  The problem is, when it gets to (100) then it automatically gives you the “Save As” pop-up and ceases to automatically append a number to the file.

Image (100).pdf marks the highest number it will automatically append

Solution: Delete or move the Image (1).pdf through Image (100).pdf files from your default downloads folder so it can go back to automatically appending the file names.

Note: Prepare to do this every time when you’ve reached 101 saves of the same file name.

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