Gmail not sending via Apple Mail

Hi, I’m having a problem whereby when I send a gmail message from Apple Mail on my iPad there are occasions, which appear to be completely random, when the message doesn’t get sent. I don’t realise this until a couple of days later when I haven’t received an expected reply.

If I save the message to drafts and then send it, it nearly always goes without issue. However if I just hit the send button then sometimes the mail goes and other times I hear the “whoosh” but when I look in my sent box it’s not there ie it seems to have disappeared into the “ether”.

I’ve deleted and reinstated the gmail account in Apple Mail, I’ve updated the gmail app on the iPad albeit I use the mail from my Apple Mail app.

I have no idea why this is. Can anybody explain please?

iPad Air, iPadOS 16

Posted on Jun 19, 2023 06:19 AM

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Jun 19, 2023 06:50 AM in response to Russelpe

Start with initial fault finding:


What happens when you try to receive or send email? Do you see any errors - and if so, what do you see?


If email is failing to send or receive, you are likely to see indicative errors at the bottom of the mail sidebar - the wording of the error usually providing sufficient information to determine the nature of the problem.


Deleting and re-adding your email account is sometimes the easiest way to resolve a problem with a specific Mail account. After deleting the account, perform a forced restart before re-adding the email account to your iPad.


  • Delete account:

Settings > Mail > Accounts > [Your Mail Account] > Delete Account


  • Force restart the iPad:

Force restart iPad - Apple Support


  • Add Mail Account:

Settings > Mail > Add Account



Also be aware that some email providers now require the use of App Specific Passwords when accessing mail over IMAP or POP3. If this applies to your email account, you will need to generate a unique password for your iPad email account - that will differ from your normal Account Password. As examples - AOL, Yahoo, Google, Microsoft all use App Specific Passwords when using anything other than their own email client Apps.


If you need to generate an App Specific Password, you’ll need to log-in to your Mail Providers account management webpage - using a web browser - and generate the Password from the appropriate account security page.


More information about AOL’s App Specific Passwords can be found here:

https://help.aol.com/articles/allow-apps-that-use-less-secure-sign-in?guccounter=1


For Yahoo, more information can be found here:

https://help.yahoo.com/kb/SLN27791.html


For Gmail:

https://support.google.com/mail/answer/185833?hl=en-GB


Microsoft:

https://support.microsoft.com/en-us/account-billing/using-app-passwords-with-apps-that-don-t-support-two-step-verification-5896ed9b-4263-e681-128a-a6f2979a7944

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Gmail not sending via Apple Mail

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