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Connecting to Gmail "Securely"

Western Digital Drives - The Preferred Drives of FreeNAS and TrueNAS CORE

nello

Patron
Joined
Dec 30, 2012
Messages
351
I use a Gmail account for email notifications from my FreeNAS server.

I recently reviewed my security settings on my Gmail account and found a setting called "Allow Less Secure Apps":
Sign-in___security.png


https://myaccount.google.com/security?pli=1#connectedapps

Some non-Google apps and devices use less secure sign-in technology, which could leave your account vulnerable. You can turn off access for these apps (which we recommend) or choose to use them despite the risks.​

I turned off access for "less secure apps" and lo and behold, message from my FreeNAS server no longer work and Gmail reports that it prevented an insecure app from using my account. After allowing "less secure apps," messages from my FreeNAS server are flowing.

Does anyone know why FreeNAS connections to Gmail's SMTP server are apparently considered "less secure"?

Is there a way to make FreeNAS use of Gmail's SMTP servers more secure (from Google's perspective anyway)?
 

Yatti420

Wizard
Joined
Aug 12, 2012
Messages
1,437
Last edited:

Jailer

Not strong, but bad
Joined
Sep 12, 2014
Messages
4,800
Is there a way to make FreeNAS use of Gmail's SMTP servers more secure (from Google's perspective anyway)?

Follow @Yatti420 advice and set up an app specific password for FreeNAS. It works flawlessly.
 

Yatti420

Wizard
Joined
Aug 12, 2012
Messages
1,437
Yes.. Also because you'll be using 2 factor authentication..Not only is it more secure it removes that unsecure option from google.. I don't have the ability to even see it on my security page.. I carry encrypted google codes incase i forget my password or mess stuff up for accessing account via other pcs... I don't have any other pc in my trusted lists.. for example all normal devices sign in normally .. I don't let them bypass anything.. If you configure specific (within browser) cookies etc it'll let your devices stay signed in.. With minimal loss to security.. Depends how security crazy you are.. I use noscript and adblock etc.. etc..

Also to note sir as a reminder I note your motherboard isn't using ECC ram.. Just beware of the caveats of that..
 
Last edited:

Elliott

Dabbler
Joined
Sep 13, 2019
Messages
40
I think Google wants everyone to use OAuth2. Not sure if there is a way to make this work in FreeNAS though.
Adding an "app password" will make Google stop nagging you, but it doesn't really make the connection any more secure. I believe we are using TLS either way.
 

BlueNGray

Dabbler
Joined
Nov 27, 2019
Messages
12
On 16 December, 2019, I received an e-mail from the "G-Suite Team" indicating that effective 21 February 2021, all Less Secure Apps will be locked out, including all password-based authentication, and the only way to connect to Google servers is by Oauth2. As I understand it, this means that using an App Password will no longer work.

Are there plans in place to deal with this restriction?
 
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