UserAgent: Mozilla/5.0 (Windows NT 10.0; Win64; x64) AppleWebKit/537.36 (KHTML, like Gecko) Chrome/65.0.3325.181 Safari/537.36

Example URL:

Steps to reproduce the problem:
1. Download a file 101 times with the same name into the same folder, having the download setting to prompt for a save location disabled.
2. Your last file should be named FILENAME(100). attempt to download the same filename/file a 102nd time
3. Be prompted to name your saved file despite chrome settings saying all files will auto-download to a specified folder.

What is the expected behavior?
Windows doesn't have a hard limit to how many FILENAME(1), FILENAME(2) etc copies you can make, at least not that I saw. Chrome should either number past (100) or put up a small warning that too many files share the same name and to clear out their destination folder for auto-downloading.

What went wrong?
User was prompted to designate a download location rather than auto-naming a duplicate named file for the 102nd time. User had the setting to auto-download to a folder location, but was still getting a prompt.

Did this work before? N/A 

Chrome version: 65.0.3325.181  Channel: stable
OS Version: 10.0
Flash Version: 

If you thought a user wouldn't download the same file 100+ times, you were wrong. :P
I'd request you up the limit to 999 or just put in a warning that the duplicate limit is 100. Thanks!