Cannot send from mac mail

[https://id.mayfirst.org/rebeccabray]

Hello,

I use 3 different mayfirst email accounts.

I have set them up in my mac mail. I am able to receive email there but not send. When I try to send from any of the accounts, I get a window that says: Cannot send message using the server mail.mayfirst.org... Relay access denied.

Also, on the webmail browser, I am able to send from 2 of the accounts but not the third one. When I login to that account, a popup window asks me to verify my sender identity. The email address in the popup is incorrect (directors@… instead of directors@…). When I try to send an email from that webmail account, it says SMTP Error 535.

[https://id.mayfirst.org/rebeccabray]

screenshot of mac mail settings

[https://id.mayfirst.org/rebeccabray]

screenshot of mac mail settings advanced

[https://id.mayfirst.org/jaimev]

Regarding mac mail: So in the second screen shot I see you are using TLS and imap you could change that to 993, however these settings relate to receiving mail and shouldn't affect sending e-mail, using port 143 there probably just uses STARTTLS as opposed to TLS directly for you IMAP connection. Outgoing mail is handled by the smtp settings in the first screen shot and apparently you can only choose the outgoing server, I assume it must use the same "User name" to login to the smtp server which is correct in this case. In our logs I do not see an attempt to connect from your client. Can you try again note the exact time you are attempting to send.

Regarding sending from roundcube: The sender identity can be changed at any time.

Click Settings (gear icon) in top right hand corner Under the Settings column, click Identities Click on the identity that is there and your info will show up on the right hand side Edit your info appropriately, especially the Email address. Click Save.

However, the identity setting would not be the reason you are unable to send the e-mail. Are you logging as "directors" in all lowercase?

[https://id.mayfirst.org/rebeccabray]

Thanks. On the web browser, switching to lower case 'directors' seemed to have solved the problem there - can send now.

On mac mail, just tried sending from rebecca@… at 9:22 and from Directors at 9:23, and from manager at 9:24.

Rebecca

[https://id.mayfirst.org/jaimev]

Ok, I think I do see attempts to connect in the logs that correspond to those times, however there is something strange about how your Mac mail client is attempting to authenticate to the server and it being rejected promptly. It does not appear to be presenting your authentication credentials to the server as it should.

Jan 27 09:22:55 paulo postfix/smtpd[4978]: NOQUEUE: reject: RCPT from unknown[69.138.8.153]: 454 4.7.1 <bray.rebecca@gmail.com>: Relay access denied; from=<rebecca@artisticactivism.org> to=<bray.rebecca@gmail.com> proto=ESMTP helo=<[192.168.0.21]>
Jan 27 09:23:44 paulo postfix/smtpd[4978]: NOQUEUE: reject: RCPT from unknown[69.138.8.153]: 454 4.7.1 <bray.rebecca@gmail.com>: Relay access denied; from=<directors@artisticactivism.org> to=<bray.rebecca@gmail.com> proto=ESMTP helo=<[192.168.0.21]>
Jan 27 09:24:46 paulo postfix/smtpd[4951]: NOQUEUE: reject: RCPT from unknown[69.138.8.153]: 454 4.7.1 <bray.rebecca@gmail.com>: Relay access denied; from=<manager@artisticactivism.org> to=<bray.rebecca@gmail.com> proto=ESMTP helo=<[192.168.0.21]>

Are there any other options, screenshots that you can share with me to help debug this?

[https://id.mayfirst.org/rebeccabray]

Error on send

[https://id.mayfirst.org/rebeccabray]

mail servers options

[https://id.mayfirst.org/rebeccabray]

Connection doctor

[https://id.mayfirst.org/rebeccabray]

Yes, thanks - I just uploaded 3 more screenshots.

[https://id.mayfirst.org/jaimev]

In the second screenshot you just uploaded, can you show me what options are available under the Advanced tab?

[https://id.mayfirst.org/rebeccabray]

advanced tab

[https://id.mayfirst.org/rebeccabray]

Yes, here you go

[https://id.mayfirst.org/jaimev]

Ok, so I have an idea. I will link to the corresponding screenshots you've sent me to help explain.

In that smtp server list you have four different mail.mayfirst.org profiles. Let's try and distinguish those by adding something to the description field for each one. So for each profile in the server list fill in the ​| description field with the email address that corresponds to the user and password you've entered in its corresponding ​| advanced tab fields. Also in the advanced tab set the port number to 465 for each of these. Since you only really have three accounts so far you should end up with at least one extra smtp profile for mail.mayfirst.org from the list and you can delete that one.

Then for each of mail ​| accounts make sure you've selected the corresponding profile as the outgoing smtp server.

[https://id.mayfirst.org/rebeccabray]

Yes!! It worked. Thank you so so much Jaime. You're the best.