Why isn'tmy Apple mail syncing with the Gamil server?

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Hi,
I'm guessing this isn't a new question but I have not been able to find it in a search.
I use Apple Mail and have a Gmail account (IMAP). I recently received a message that my Gmail storeage is nearly full and when I checked, there are tens of thousands of messages in Trash going back years. These do not appear on my Mac. The Gmail screen has this on the top: "Messages that have been in Trash more than 30 days will be automatically deleted" but this has obviously not happened. I've posted on the Gmail Community site but have not received a reply. I've tried googling how to delete in bulk but have not found anything that works. Deleting on the Gmail site, 100 messages at a time, is not practical.

Does anyone know why deleting on my Mac is not syncing with the Gail server and how to fix it? Or, how to delete on the Gmail site in bulk?

Thanks.

Mark
 

Raz0rEdge

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Login to Gmail, go to the Trash folder and click this link if you see it.

Screenshot 2025-05-20 at 1.53.55 PM.png
 
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Login to Gmail, go to the Trash folder and click this link if you see it.

View attachment 40361
Sorry, I wasn't clear enough. My understanding is that if I delete all emails on the Gmail server that will also delete all emails on my Mac. I want to destroy only the older emails, say pre-June 2024.
 

Rod


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Regardless of why gmail is not deleting your "older than 30 days" BIN contents Ashwin's suggestion will solve the immediate problem as I just did myself below. It's just the Bin I'm emptying not All Mail.:


Screenshot 2025-05-21 at 09.06.52.png

Screenshot 2025-05-21 at 09.07.25.png

Screenshot 2025-05-21 at 09.07.49.png

All gone.

Why haven't the old messages been deleted automatically?
"When a user deletes an email in Gmail, it is moved to the Trash folder and remains there for 30 days before being permanently deleted. If you find that messages are not being deleted after 30 days, it could be due to a misunderstanding of the process or a specific issue with your account."

For a (much) more detailed explanation of how to use gmail on Apple Mail correctly see the "2 Answers" reply on this page:


Alternatively use a different email client to Apple Mail, it has never played nicely with Google and probably never will.
 
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Regardless of why gmail is not deleting your "older than 30 days" BIN contents Ashwin's suggestion will solve the immediate problem as I just did myself below. It's just the Bin I'm emptying not All Mail.:


View attachment 40362

View attachment 40363

View attachment 40364

All gone.

Why haven't the old messages been deleted automatically?
"When a user deletes an email in Gmail, it is moved to the Trash folder and remains there for 30 days before being permanently deleted. If you find that messages are not being deleted after 30 days, it could be due to a misunderstanding of the process or a specific issue with your account."

For a (much) more detailed explanation of how to use gmail on Apple Mail correctly see the "2 Answers" reply on this page:


Alternatively use a different email client to Apple Mail, it has never played nicely with Google and probably never will.
I guess I'm having a bad couple of days, as I used to think I write clearly but rereading my posts I see that I've done a bad job. I'll try again. What I want to do is to delete the tens of thousands of emails sitting in the Trash folder of the Gmail server, but only those that are more than one year old. I've read that if I click the "delete all" link it will empty the entire Trash folder both on the gmail server and on my Mac.
With the Trash folder highlighted I've been able to isolate the emails to be deleted by entering "Before:2024-05-20" in the seaerch bar but then am unable to find a way to permanently delete them.

Thank you for the link to the other 2 questions, I will read them tonight.

Mark
 
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Rod


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Right Mark, I get it now. The answer may well be in the article I linked, there's a lot of content.
Obviously this would not have been as issue if gmail had deleted everything over 30 days old automatically. As said Apple Mail doesn't always initiate the right responses from Google and when you think they are really two competing companies with their own operating systems it's really not surprising. If you were to use the Gmail app on macOS you probably wouldn't encounter any problems. Both are quite complex apps essentially designed for different platforms.

I use Spark Desktop myself and have no problems with iCloud, Microsoft, Gmail, Yahoo and a couple of others. My thinking is that an email client purposely designed to handle a full range of IMAP accounts will not be biased towards any one OS. I get, on average, one update a week on Spark the most recent being compatibility with the Microsoft Calendar, so it's focus is clearly on compatibility.

How often have you seen an Apple update that improves compatibility with Google apps?
 
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With the Trash folder highlighted I've been able to isolate the emails to be deleted by entering "Before:2024-05-20" in the seaerch bar but then am unable to find a way to permanently delete them.
If they are continuous, you can just select the first one, then hold shift and select the last one. Holding gift down should select all emails in between the two you selected.
 

LoydPeterson

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I use Spark instead of Apple Mail. Much clearer behavior of emails, plus better integration with Gmail
 
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If they are continuous, you can just select the first one, then hold shift and select the last one. Holding gift down should select all emails in between the two you selected.
Thanks, but as far as I can tell, I can only highlight the emails on the page, which is limited to 100. If there is a way to highlight the first email and then jump to the last page with the shift key down, I do not know how.
 
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Right Mark, I get it now. The answer may well be in the article I linked, there's a lot of content.
Obviously this would not have been as issue if gmail had deleted everything over 30 days old automatically. As said Apple Mail doesn't always initiate the right responses from Google and when you think they are really two competing companies with their own operating systems it's really not surprising. If you were to use the Gmail app on macOS you probably wouldn't encounter any problems. Both are quite complex apps essentially designed for different platforms.

I use Spark Desktop myself and have no problems with iCloud, Microsoft, Gmail, Yahoo and a couple of others. My thinking is that an email client purposely designed to handle a full range of IMAP accounts will not be biased towards any one OS. I get, on average, one update a week on Spark the most recent being compatibility with the Microsoft Calendar, so it's focus is clearly on compatibility.

How often have you seen an Apple update that improves compatibility with Google apps?
Well Rod, as you wrote, this is a long and detailed post. I've read it several times and changed the settings indicated but so far at least, nothing has happened on the Gmail server end. What it did do though, is empty the Google Trash folder on my Mac, but strangely and happily, not the All Trash folder.
At this point I think I'm going to give up and look at another mail app. You mentioned Spark Desktop and I've also heard good things about Thunderbird. Or maybe just get an iCloud address, which I'm guessing will integrate perfectly with Apple Mail.

Thanks very much for your help.

Mark
 
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It may be that syncing trash folders on my Mac and the Gmail server may not be possible. I googled the question using Thunderbird as the example and attached is the answer I got.
If so, I now have to find out why the server's automatic delete in 30 days is not working.
 

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Rod


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In which case I think your answer probably lies in Google help. it seems like a long standing issue.
Like lots of people I imagine, I very seldom go to gmail on a browser and I don't use the gmail for Mac or iOS apps. Yesterday was the first time I've manually emptied the trash Bin for years and as it only had 80 odd trashed emails I have to assume that it is automatically being emptied and corresponds to what I trash on Spark and or Mail. I do use Mail occasionally to launch SpamSieve as this does not yet work with Spark.

One thing that did crop up in my reading was a comment from a user on Reddit, "If your Gmail trash bin is not emptying after 30 days, it might be due to a few reasons. One possible cause is using the Apple iOS Mail app to access Gmail, as there have been reports of the app deleting Gmail emails without permission and without warning." So there are some issues with the process and the fault could be on either side of the fence.
It seems like it just works for the majority of users so you may need to settle for a workaround until it either gets worse or fixes itself.
 
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Well, I do access my Gmail on my iPhone also, so maybe the problem is there. Good tip, thanks.
As for Google help, that’s where I started and received no replies. I’m glad it works for you. That tells me it’s some setting that I just have to keep searching for.
 

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