Resolved How can I empty the trash, forever?

I decided to put all Time Machine backups to the trash, except the latest one. I don’t need any of them (except the latest one obviously). I managed to clear 100 GB of space this way, which I thought was pretty good.

The problem now is, I can’t empty the trash. When I disconnect the external hard drive, it appears to be empty, but when I reconnect the HD, obviously it’s full again.

I’ve read all kinds of solution and nothing worked, and now I’m seriously annoyed, is there no big red button to delete everything? I can’t mess with this stuff anymore, argh!

EDIT: Solution can be found [URL="https://forums.macrumors.com/posts/17478808/”]here[/URL]. Topic resolved!

simsaladimbamba said:

As the Trash is stored on the volume it gets deleted on, thus ejecting the volume with the Trash on makes it look like your Trash is empty. But if you reconnect that volume again, the Trash is not empty anymore, unless you really empty the Trash when the volume with the full Trash is connected.

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Oops, I forgot to mention the most important part. I can’t empty it when the volume is connected. It goes into negative numbers and eventually nothing happens. And the trash just stays there and doesn’t move. Anywhere.

Still haven’t found a solution for that…

simsaladimbamba said:

Can this help?

You can't empty the Trash or move a file to the Trash and Solving Trash Problems

And you did mention the important part, I just did not read it carefully to reply properly.

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True, seems like I forgot what I wrote myself
As for the link, I tried everything that is written in there already, no luck…

benwiggy said:

I'm not convinced that manually deleting TM backups from the Finder is a very good idea.
If you need more space on a Time Machine volume, TM will start eating the oldest backups to make room for the new ones.

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I’m not convinced it’s a good idea either. I couldn’t find another solution however, and really wanted to get rid of these. Weirdly enough, my Time Machine doesn’t delete any old backups. Instead it’s telling me there’s not enough space anymore. Stupid thing, if there’s not enough space anymore it should delete the oldest one. At least that seems to work for everyone else. Some people sent me a page that was talking about exactly this issue, but I did not find any solution nor was able to make it delete old backups, so I was trying to delete them manually.

Bear said:

The proper way to delete a Time Machine backup is:

1. Enter time machine
2. Go to the point in time you want to delete (Do not delete the latest backup)
3. Select the icon that looks like a cog in the finder toolbar and choose "Delete Backup"

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I tried this at least a dozen times. Not sure why but it won’t work. A window once appeared that it is preparing to delete the backup. But nothing happened afterwards. Or maybe I didn’t notice? It doesn’t seem like a backup is missing, and there wasn’t anything in the trash. Maybe, however, it’s deleted right away without going to the trash at all? But still I would notice if a backup was missing.

Finally I managed to delete some backups through the Time Machine window. It just took some time and you gotta leave Time Machine after that.

Now how do I delete these backups that I manually put to the trash? I tried dragging them to the backup volume/folder again, but it says me it can’t be modified or something. Sucks, I really shouldn’t have done that

Edit: Finally, I found the solution! In case anyone lands on this thread one day, follow what the guy explains in this post. It worked perfectly for me! Thanks a lot to him