Emails are sending to gmail (allegedly) via SMTP, but I am not receiving them

[testfire10]

Hi everyone,

system specs:
supermicro X9DRH-7F
dual 2650v2 Xeon
48GB RAM
6X 8TB HGST SAS drives

I'm able to access my dataset just fine, ping the system, SSH into the system, and I believe all aspects of the network are working. I've followed a couple of the guides here to try and set up email notifications, and cannot actually receive the emails that appear to be successfully sent to my gmail account.

the From email, I've used as my email address, I'm using smtp.gmail.com for the smtp server, TLS, port 587, and my gmail creds. I do not have 2FA enabled on gmail (nor do I want to). When I click send test email, I get a notification stating that the email has been sent, but I do not receive an email to my gmail account.

I have also tried SSL using port 465, which does not work. FWIW, I am able to get emails through my Unifi network controller software using 465, and my synology NAS using same without issue.

 

[sretalla]

Check your SPAM folder.

 

[testfire10]

Check your SPAM folder.

I did that as well, along with all other folders - no dice.

 

[testfire10]

An update. Today I received about 30 or so emails from TrueNAS to my gmail account. About 20 of them were successful, and about 10 were failures. These are the messages from all the times I was sending test emails yesterday and the failures are likely the times when I was trying some different configurations. So now I have 2 questions.

1) Why did it take so long for me to receive these messages (they all appeared to be timestamped properly, but receipt was delayed by as much as 24 hrs)
2) Now when I send tests emails, once again I am not receiving them. What is taking them so long to get to me?

 

[Spearfoot]

An update. Today I received about 30 or so emails from TrueNAS to my gmail account. About 20 of them were successful, and about 10 were failures. These are the messages from all the times I was sending test emails yesterday and the failures are likely the times when I was trying some different configurations. So now I have 2 questions.

1) Why did it take so long for me to receive these messages (they all appeared to be timestamped properly, but receipt was delayed by as much as 24 hrs)
2) Now when I send tests emails, once again I am not receiving them. What is taking them so long to get to me?

FreeNAS/TrueNAS connects to the mail host you specify, transmitting email messages immediately when they're submitted. After that, the messages are out of its hands.

I have no idea why it's taking Google so long to deliver messages to your inbox on their system.

I don't use Google mail for FreeNAS/TrueNAS emails, but I do remember having to set up 'application keys' to use non-Google mail clients such as Outlook. Perhaps you need to do the same thing?

 

[testfire10]

FreeNAS/TrueNAS connects to the mail host you specify, transmitting email messages immediately when they're submitted. After that, the messages are out of its hands.

I have no idea why it's taking Google so long to deliver messages to your inbox on their system.

I don't use Google mail for FreeNAS/TrueNAS emails, but I do remember having to set up 'application keys' to use non-Google mail clients such as Outlook. Perhaps you need to do the same thing?

I read one of the common/stickied threads on here suggesting that. I use Unifi and Synology to send similar emails, and have no issues with messages coming through (immediately), and have never had to setup application keys.

 

[testfire10]

An update. I noticed after receiving a huge number of test emails that my SENT emails were also showing up in gmail, which makes sense. When I investigated these, I saw that the 'to' address was 'root@truenas.com'. I went to my root user, and changed the email address to my gmail address, and this worked when sending a test email immediately. Nowhere that I read online did I see anything about changing the email address of the root user to solve this issue... but it is working now.

 

[HarambeLives]

I had nothing but trouble using Gmail. Worse, it would work and then stop working. Of course it stops working when you need it most!

Get a domain and use something like SendGrid, will be a much better solution. Personally I subscribe to O365 Business Basic for $5/mo. Best money I ever spend, having my personal email with my own domain, and a full Exchange setup around it