SMTP Fails with GMail on MacOS/IOS

I currently utilize 2 GMail accounts on with IOS and MAC Mail. One of the accounts has just stoped working for SMTP. The other account works fine.

 The effect is is the same on both IOS and MAC.  

"Cannot Send the Message Using the Server xxxxx.gmail.com" - MAC

"Cannot Send Mail. The connection to the outgoing server smtp.gmail.com failed" - IOS


I have tried all the usual remedies.

Remove 2 Factor Auth

Enable Less Secure Apps

Deleted and Added back the Account

Set up the account as IMAP Only

Cleared Captcha.


All without effect.

The logs from the connection doctor indicate the following.



WROTE Nov 04 09:21:25.914 [kCFStreamSocketSecurityLevelTLSv1_2] -- host:smtp.gmail.com -- port:587 -- socket:0x600003b95200 -- thread:0x60000026fe00

AUTH LOGIN


READ Nov 04 09:21:25.958 [kCFStreamSocketSecurityLevelTLSv1_2] -- host:smtp.gmail.com -- port:587 -- socket:0x600003b95200 -- thread:0x60000026fe00

334 VXNlcm5hbWU6


WROTE Nov 04 09:21:25.958 [kCFStreamSocketSecurityLevelTLSv1_2] -- host:smtp.gmail.com -- port:587 -- socket:0x600003b95200 -- thread:0x60000026fe00

QnJpYbWFW4uSW4zNEBnG9nYpbC5jb20=


READ Nov 04 09:21:26.004 [kCFStreamSocketSecurityLevelTLSv1_2] -- host:smtp.gmail.com -- port:587 -- socket:0x600003b95200 -- thread:0x60000026fe00

334 UGFzc3dvcmQ6


WROTE Nov 04 09:21:26.004 [kCFStreamSocketSecurityLevelTLSv1_2] -- host:smtp.gmail.com -- port:587 -- socket:0x600003b95200 -- thread:0x60000026fe00

*


READ Nov 04 09:21:26.049 [kCFStreamSocketSecurityLevelTLSv1_2] -- host:smtp.gmail.com -- port:587 -- socket:0x600003b95200 -- thread:0x60000026fe00

501 5.5.2 Cannot Decode response e10sm3749582qtx.66 - gsmtp



Then it fails with too many login attempts.

Every now and then, the account will work again for a short period.


Downloading the GMail app for IOS works correctly every time.

Using the Web App for GMail also works fine.


Any help would be appreciated.

MacBook Pro 15″, macOS 10.15

Posted on Nov 7, 2021 12:32 AM

Reply

Similar questions

3 replies

Nov 7, 2021 4:13 AM in response to NESSINC

NESSINC wrote:

I currently utilize 2 GMail accounts on with IOS and MAC Mail. One of the accounts has just stoped working for SMTP. The other account works fine.
 The effect is is the same on both IOS and MAC.  
"Cannot Send the Message Using the Server xxxxx.gmail.com" - MAC
"Cannot Send Mail. The connection to the outgoing server smtp.gmail.com failed" - IOS

I have tried all the usual remedies.
Remove 2 Factor Auth
Enable Less Secure Apps
Deleted and Added back the Account
Set up the account as IMAP Only
Cleared Captcha.

All without effect.
The logs from the connection doctor indicate the following.


WROTE Nov 04 09:21:25.914 [kCFStreamSocketSecurityLevelTLSv1_2] -- host:smtp.gmail.com -- port:587 -- socket:0x600003b95200 -- thread:0x60000026fe00
AUTH LOGIN

READ Nov 04 09:21:25.958 [kCFStreamSocketSecurityLevelTLSv1_2] -- host:smtp.gmail.com -- port:587 -- socket:0x600003b95200 -- thread:0x60000026fe00
334 VXNlcm5hbWU6

WROTE Nov 04 09:21:25.958 [kCFStreamSocketSecurityLevelTLSv1_2] -- host:smtp.gmail.com -- port:587 -- socket:0x600003b95200 -- thread:0x60000026fe00
QnJpYbWFW4uSW4zNEBnG9nYpbC5jb20=

READ Nov 04 09:21:26.004 [kCFStreamSocketSecurityLevelTLSv1_2] -- host:smtp.gmail.com -- port:587 -- socket:0x600003b95200 -- thread:0x60000026fe00
334 UGFzc3dvcmQ6

WROTE Nov 04 09:21:26.004 [kCFStreamSocketSecurityLevelTLSv1_2] -- host:smtp.gmail.com -- port:587 -- socket:0x600003b95200 -- thread:0x60000026fe00
*

READ Nov 04 09:21:26.049 [kCFStreamSocketSecurityLevelTLSv1_2] -- host:smtp.gmail.com -- port:587 -- socket:0x600003b95200 -- thread:0x60000026fe00
501 5.5.2 Cannot Decode response e10sm3749582qtx.66 - gsmtp


Then it fails with too many login attempts.
Every now and then, the account will work again for a short period.

Downloading the GMail app for IOS works correctly every time.
Using the Web App for GMail also works fine.

Any help would be appreciated.


Deleting a problem account and adding it back in to sort anomalies


Remove email accounts in Mail on Mac

https://support.apple.com/en-lamr/guide/mail/mlhl9eb9408c/15.0/mac/12.0


Add email accounts in Mail on Mac - Apple Support

https://support.apple.com/en-lamr/guide/mail/mail35803/mac



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SMTP Fails with GMail on MacOS/IOS

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