- Search for the messages you want to delete
example: label:mylabel
- Click the checkbox at the top to select all of the conversations on the page
You'll get a message similar to:
All 100 conversations on this page are selected. Select all 75432 conversations
The latter portion is a clickable link. Click it.
- Now all your messages matching the search are "checked"
- Click "Delete"
It may take a few minutes to move them all to Trash.
If you get an error, you're probably simply trying to do too many at once for your local browser, network, and/or server to handle. (It shouldn't happen, but apparently it does for you.) Try breaking your search up into smaller, but manageable, chunks. There are several advanced search operators you can use. You might try one of the time-based operators, so you can do something like this:
Search for all the messages with your label that are older than a year:
label:mylabel older_than:1y
Then follow the other steps above.