I'm specifically thinking of the tags
perl-lwp these both mean exactly the same thing and as far as google is concerned
lwp has only one meaning. I'm wondering if it would be appropriate to retag posts to only one of these 2 so in the end only one exists?
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Assuming [lwp] and [perl-lwp] are actually used interchangeably, it's definitely ok and happens all the time; there's actually a couple 10k tools specifically for finding new synonymous tags and easily retagging them, and a moderator tool to merge tags immediately. If there's a lot of retags needed, you can request here that a moderator do the retagging instead with that tool (just tag the question [retag-request]). You can also propose a tag synonym on the info page of one of the tags; there's more info about tag synonyms on the blog