We generally flag rude or unfriendly comments for deletion. But sometimes moderators may miss those comment flags when comment section is a place of conversation and many other normal comments are posted under a question or answer. When that happens, moderators move (when Community user notifies there is a long conversation happening) comments to chat room.

Whole comment conversation is moved to chat room, comment flags are marked as helpful automatically and those rude/unfriendly comments not deleted but also moved along with other normal comments and saved as chat messages. Our comment flags are marked helpful but rude comments are handled individually.

When those conversations are moved, can we flag those chat messages for moderator intervention again to indicate unfriendly content or spam/offensive flag if that is previously an unhandled rude comment? Or should we leave those messages to avoid further prolongation?

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    You mean flagging them in chat? – Catija Jul 27 at 3:04
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    @Catija Yes, using a chat flag for rude messages. – Nog Shine Jul 27 at 3:08

I recommend caution in flagging the messages in chat, even with a moderator flag rather than a general spam/abusive flag.

I'd recommend that you flag the post the comments were on for moderator attention and point out the comments are in chat despite having been flagged as rude and request that they be deleted from chat. This will ensure that only the mods from that site have to deal with the flags.

If you flag for moderator attention, it will draw any mods who are online to the room, not only the mods on the site. This may bring more attention to the room than necessary, particularly if the room is currently quiet.

Another option would be, if you have access to the moderators for the site in chat. Some mods are very active in chat or even have a mod-specific public room for their site. If this exists, and you can see they're recently active, you can try pinging one of them in that room and asking them to address the issue.

If the content is particularly terrible and you feel it needs immediate action and these methods don't seem quick enough, you can use a custom chat flag but if the room is currently quiet, it's unlikely to need immediate attention.

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    The issues in your second and third paragraph are non-issues on Stack Overflow and here on Meta.SE, due to them having site-specific chat servers. – Sonic the Reinstate Monica-hog Jul 27 at 3:38

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