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Seems like every time I open the dev console these days I get this message:

The Developer Console didn't set the DEVELOPER_LOG trace flag on your user. Having an active trace flag triggers debug logging. You have 403 MB of the maximum 250 MB of debug logs. Before you can edit trace flags, delete some debug logs.

I've had to manually query ApexLog using the Tooling API and delete the existing logs every time for new logs to start recording again.

I did hear somewhere that SF switched from a time limit on debug logs to a size limit... But is there a setting change that allows SF to go back to deleting the oldest logs when the size limit is reached?

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Looks like this was a duplicate. Answer seems to be just manually deleting for now. Here is a thread with more info: Maximum log level exceeded in Developer Console

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