I tried to find a duplicate bug report, but surprisingly couldn't. Bug 6964 is similar-ish.

(In reply to Jon from comment #0)

When managing a watchlist, I find it frustrating that I cannot find why I
added them.

I think the watchlist should have record a timestamp of when it was added to
the watchlist.

I'm not sure a timestamp will/can answer "why". Annotations might, though. There's probably no reason we can't have both. :-)

Created attachment 15349
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Imagining something vaguely like this, where its still one click, but you have the option of adding a comment or tagging/categorizing the item, date would just be added automatically and segmented into logical chunks, this hour, today, yesterday, this week, last week, this month, last month, etc…

Attached:

swalling wrote:

(In reply to Jared Zimmerman (WMF) from comment #2)

Created attachment 15349 [details]
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Imagining something vaguely like this, where its still one click, but you
have the option of adding a comment or tagging/categorizing the item, date
would just be added automatically and segmented into logical chunks, this
hour, today, yesterday, this week, last week, this month, last month, etc…

Related to your ideas: https://www.mediawiki.org/wiki/Requests_for_comment/Support_for_user-specific_page_lists_in_core

That kind of refactor of the watchlist table would make it a lot easier to have other kinds of page lists.

I do think this is a good direction to go in, but we should be careful. This reminds of Twitter lists: enormously powerful if curated heavily, but most users are not willing to put in this effort. I think a redesign of watchlists to be easier to read/filter as they exist now could be a good first step without requiring a refactor of how the data is stored.

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Moving to "Triaged but Future" because this a large amount of work and database changes for a relatively low impact vs. the user retention work that Growth team will be doing.

@Addshore

Just like that, without even a comment?

In T67187#6597749, @Scott wrote:

@Addshore

Just like that, without even a comment?

Added comments, sorry I didn't see this ticket attached to the others.
From the other tickets:

I'm declining this as the task creator as this was primarily created for T100508: Watchlist expiry: Watch pages for a specified time frame (2013) which has since been done by other means.
If someone else wants to take on this task for T67187: Show when pages were added to watchlist for example then please reopen it (and perhaps adjust the ticket chain)

@Addshore OK, great. Thanks for the info 👍