Thanks to an Windows File Manager (WinFile.exe) which was released as an open-source project by Microsoft about 2 years ago, you can achieve this easily.
WinFile is free and builds available for Windows 7,10 here - https://github.com/Microsoft/winfile
Testing with WinFile to delete paths that are too long on network share.
You just have to map the network share to a drive letter, then proceed to delete files. This will only work on Microsoft server shares. Linux/Mac/other share's are not supported for path too long.
"A Transport and there is a great amount of Handling Unit Type of test_Thingy.docx"
as 8.3 DOS short name might be
"ATRANS~1.DOCX"
Conclusion:
Sorry, you cannot use WinFile to delete path too long.
TL;DR
WinFile does not natively handle paths longer than 260 characters, even with 8.3 short names. It inherits the traditional Windows API limitations, and while modern Windows supports long paths if enabled, WinFile itself was not updated to fully support them.
Solution:
To find many paths that are too long and automate a fix, use Path Too Long Auto Fixer (PTLAF) - a free demo is available. PTLAF supports Network Shares and Linux paths up to 4096 characters long.It can delete paths on UNIX, Mac and other shares!


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