Send test mail using Gmail help

chickennuggets

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Jun 20, 2020
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I am setting up and using Freenas for the first time. I was following this guide at https://www.ixsystems.com/community...-getting-freenas-to-email-you-in-gmail.22517/ , and I need some help on figuring out how to resolve this error after configuring email in root, setting up in System -> Email, and creating app password in Gmail to get around 2 factor authentication:
Code:
[EFAULT] Failed to send email: [Errno 65] No route to host


System Specs
Freenas version 11.3-U3.2
Motherboard: Supermicro X11SSM-F-O
CPU: Intel Pentium G4400
RAM: 64 GB
Boot Drive: 1x 120 GB Kingston A400 SSD
Drives: 2x 1.92GB Samsung sm863a SSD in mirror
All drives connected with direct SATA connection
Network cards: built in motherboard

I'm not very familiar with networking stuff, so I do need a little bit of walkthrough.
 

diedrichg

Wizard
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Dec 4, 2012
Messages
1,319
Hi. I'm the author of that thread, are the steps not correct? If you follow them, are you able to get the one-time password step? From there it's just plugging in the required information into FreeNAS.
 

Samuel Tai

Never underestimate your own stupidity
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Apr 24, 2020
Messages
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Don’t overlook mundane things like network settings. Under Network->Network Summary, do you have a default gateway, and DNS servers showing? Both would be required for sending to Gmail.
 

chickennuggets

Dabbler
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Jun 20, 2020
Messages
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Hi. I'm the author of that thread, are the steps not correct? If you follow them, are you able to get the one-time password step? From there it's just plugging in the required information into FreeNAS.
Yes, I have the one time password created.

Don’t overlook mundane things like network settings. Under Network->Network Summary, do you have a default gateway, and DNS servers showing? Both would be required for sending to Gmail.
Default Routes (same as gateway?) and nameservers are present - I didn't touch those fields and were already there by itself.
 

Samuel Tai

Never underestimate your own stupidity
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If you have IPv6 addresses active, you also need IPv6 default gateways and DNS servers.
 

chickennuggets

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If you have IPv6 addresses active, you also need IPv6 default gateways and DNS servers.
I don't think I have any IPv6 active, from looking through my router settings.
 

Samuel Tai

Never underestimate your own stupidity
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Does Network->Network Summary show IPv6 addresses?
 

chickennuggets

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Samuel Tai

Never underestimate your own stupidity
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What do you get from running nslookup smtp.gmail.com?
 

chickennuggets

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Samuel Tai

Never underestimate your own stupidity
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That's the problem. DNS is sometimes returning the IPv6 address for smtp.gmail.com, and you don't have an IPv6 path out on your router.
 

chickennuggets

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That's the problem. DNS is sometimes returning the IPv6 address for smtp.gmail.com, and you don't have an IPv6 path out on your router.
I see...Thank you so much for your help! Messing with IPv6 configurations on my router is a little beyond what I'm comfortable with. The reason I was setting up email in the first place was so that I can get warnings about my drive health. I'll just run smartctl every once in a while manually to take care of that for now.
 

Samuel Tai

Never underestimate your own stupidity
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You could run dnsmasq in a jail, and configure it to filter out IPv6.

 

chickennuggets

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Jun 20, 2020
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You could run dnsmasq in a jail, and configure it to filter out IPv6.

Thank you for pointing me to the right direction. I will need to do some reading and learning, then come back to this. This is going beyond the scope of my capabilities. I appreciate your time and effort!
 

glauco

Guru
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Jan 30, 2017
Messages
524
You could try and disable all IPv6 settings on your router and see if that helps.
 

KevDog

Patron
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Nov 26, 2016
Messages
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Hmm, I curious for experimentation sake if he would use a different resolver such as 1.1.1.1 or 1.1.1.2, and then query smtp.gmail.com if he would receive ipv6 addresses? If not, cant ipv6 just be deactivated at the router level?
 

subhuman

Contributor
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Nov 21, 2019
Messages
121
Hmm, I curious for experimentation sake if he would use a different resolver such as 1.1.1.1 or 1.1.1.2,
I was just going to suggest that. Any of the following should work
4.2.2.3
8.8.4.4
208.67.222.222
 

esamett

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May 28, 2011
Messages
345
Hello: I have previously successfully used gmail with my FreeNAS-11.2-U7 production system. I just logged on and saw error messages from August 2020. I sent a test message and got: "Your test email could not be sent: [EAUTH] Authentication error (535): b'5.7.8 Username and Password not accepted. Learn more at\n5.7.8 https://support.google.com/mail/?p=BadCredentials m15sm3231iow.9 - gsmtp "

Searching the forum and google I saw a technique for setting up app specific passwords. However I do NOT have two factor authentication set up so the option is not available.

Can someone enlighten me as to what may have happened to gmail and how I can fix it. I am happy otherwize with my current build and would rather not update if not needed.

Thank you in advance.
 

esamett

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May 28, 2011
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345
addendum: I originally succeeded with "SSL". Based upon a forum post I swiched to "TLS" without change in error message.
 

diedrichg

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Dec 4, 2012
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