Off-topic? Best practice to sync long paths to filesystems where path length is limited?

Question

I first wanted to post this question on Stackoverflow, then thought Programmers is more appropriate, now hesitating.

Is the question below on-topic here, or better on Stackoverflow, or elsewhere?

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I wrote a sync tool to synchronize folders/files from Alfresco to Windows.
PROBLEM:

• In Alfresco, /files/can/have/very/very/very/long/filepaths/like/this.txt
• In Windows. a path can not be more than 255 characters.

In addition to telling the user there is a problem, what is the best practice in such a case?

1. Shorten the file's name?
2. Skip the file?
3. Create a sort of "folder's carriage return", a special folder from which the path can continue?
4. Something else?

Answer 1

In my opinion this is an on topic question as long as you begin with needing help designing the appropriate behavior for the system.