On Thursday 26 September 2024 22:11:20 BST Dale 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. 

STOP RIGHT THERE!

You may not have a mail application configuration problem after all (ssmtp/
msmtp), but you definitely have a network/server connectivity problem.  You 
need to sort out the network connection first, before you look at your smtp 
client configuration.


> 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
> time=32.1 ms
> 64 bytes from rq-in-f108.1e100.net (142.250.115.108): icmp_seq=2 ttl=53
> time=45.0 ms
> 64 bytes from rq-in-f108.1e100.net (142.250.115.108): icmp_seq=3 ttl=53
> time=39.3 ms
> ^C
> --- smtp.gmail.com ping statistics ---
> 3 packets transmitted, 3 received, 0% packet loss, time 1998ms
> rtt min/avg/max/mdev = 32.062/38.776/45.017/5.299 ms
> root@Gentoo-1 / # ping 142.251.116.108
> PING 142.251.116.108 (142.251.116.108) 56(84) bytes of data.
> 64 bytes from 142.251.116.108: icmp_seq=1 ttl=53 time=30.4 ms
> 64 bytes from 142.251.116.108: icmp_seq=2 ttl=53 time=56.0 ms
> 64 bytes from 142.251.116.108: icmp_seq=3 ttl=53 time=30.6 ms
> ^C
> --- 142.251.116.108 ping statistics ---
> 3 packets transmitted, 3 received, 0% packet loss, time 2000ms
> rtt min/avg/max/mdev = 30.351/38.988/56.049/12.063 ms
> root@Gentoo-1 / #

So you can access the server, but not connect to the port.

Can you connect to ports 25, or 465?

Can you connect to 'smtp-relay.gmail.com' instead?

If you cannot see an open port, then either your network is misconfigured, or 
you've annoyed Google enough to block your access to their smtp service.


> What silly boo boo did I make this time???? 
> 
> >> I am connected through a VPN but Seamonkey works fine.  I can check and
> >> send email there,

Ah!  I have found Google logs your IP address and when this changes they may 
choose to block your connection to their service.  Often it sends you a 
message in your backup email address/phone asking you to confirm if the device 
and new IP address you are trying to connect from is you and yours.

Throwing a VPN in the works may trigger the above security (re)action, when 
your client is using an 'App Password' token, as opposed to the full OAUTH2 
exchange.


> 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. 

Google's modus operandi is arguably predicated on recording your data, your 
location, your movements, your purchases, your contacts, your written/spoken 
word, your interests, your thoughts, etc.  Selling advertisements is a 
monetisation mechanism to facilitate the high cost of their operation.  They 
are not unique in this endeavor, other Big-Tech quasi-monopolies are 
performing the same role.  The offer of 'free' internet services is the 
honeypot used to attract footfall.