Grant Edwards wrote:
> On 2024-09-26, Dale <rdalek1...@gmail.com> wrote:
>
>> root@Gentoo-1 / # telnet smtp.gmail.com 587
>> Trying 142.251.116.108...
>> Trying 2607:f8b0:4023:1000::6c...
>> telnet: Unable to connect to remote host: Network is unreachable
>> root@Gentoo-1 / #
>>
>> Can't connect. Well, that explains a lot. It can't reach anything to
>> log into. It looks like it is trying both IPv4 and v6. So, I used
>> ping. It works there.
>>
>> root@Gentoo-1 / # ping smtp.gmail.com
>> PING smtp.gmail.com (142.250.115.108) 56(84) bytes of data.
>> 64 bytes from rq-in-f108.1e100.net (142.250.115.108): icmp_seq=1 ttl=53
> Those commands are using two different IP addresses.
>
> It's not uncommon that DNS resolvers for heavily used services rotate
> through a pool of addresses, but for testing purposes you should pick
> a single IP address.
>
>>>> I am connected through a VPN but Seamonkey works fine. I can check and
>>>> send email there,
>>> Do you mean can send email via Gmail's SMTP server using Seamonkey?
>>>
>>> How are the SMTP server settings configured in Seamonkey?
>>>
>>> Is it using Oauth2 or an app password?
>> I checked, It is using Oauth2. I had to change it a good while back
>> but I think SMART could still send emails for a while after that.
> Is it using the same port number as msmtp?
>

It says port 465 but it is using Oauth2 if that matters.  I'll admit,
the last time I got this working, I followed a guide and it just
worked.  Once it worked, I left it alone.  I was scared that if I
touched it, it would stop working.  LOL 

I changed the config to port 465 and it still failed with this. 


Sep 26 19:04:26 Gentoo-1 smartd[18737]: Executing test of <mail> to root ...
Sep 26 19:04:36 Gentoo-1 msmtp[18815]: host=smtp.gmail.com tls=on
auth=off from=rdalek1967<at>gmail.com recipients=root errormsg='the
server sent an empty reply' exitcode=EX_PROTOCOL
Sep 26 19:04:36 Gentoo-1 smartd[18737]: Test of <mail> to root produced
unexpected output (65 bytes) to STDOUT/STDERR:
Sep 26 19:04:36 Gentoo-1 smartd[18737]: mail: cannot send message:
Process exited with a non-zero status
Sep 26 19:04:36 Gentoo-1 smartd[18737]: Test of <mail> to root: failed
(32-bit/8-bit exit status: 256/1)


It repeated that several times before stopping. 


>>> I just did a quick test, and sending via smtp.gmail.com using an app
>>> password worked fine from mutt.  I don't have msmtp set up at the
>>> moment.
>> That is true but why buy one if you can't run it? LOL This is yet
>> another reason I want to switch from Gmail. They nothing but nosy
>> anyway. I think it is common knowledge that they scan all emails and
>> use the info for various things, including ads, which I block by the
>> way.
> There's nothing wrong with Gmail. The app password feature works
> exactly as documented, and is definitely the right way to provide
> authentication for "dumb" programs that don't know how to do OAUTH2.
>
>
>

I still don't like all the snooping they do.  Basically, I just don't
trust Google, with a lot of things. 

Dale

:-)  :-) 

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