sSMTP gives 550 error every time I try to email someone

I’ve been trying to set up a script where it sends the contents of a text file to my email: benthetechguy@yahoo.com. I set up sSMTP with the email: executeorder66@yahoo.com. What i’m trying to do is send the contents of the file /home/ben/update from executeorder66@yahoo.com to benthetechguy@yahoo.com. I’m using the command ssmtp benthetechguy@yahoo.com < update. Every time I try it, it gives me the error 550 Request failed; Mailbox unavailable. I’ve tried to send it to yahoo emails, gmail emails, outlook emails, and even an AOL email! I’ve also tried two different yahoo emails and a google email to send it with. I’ve looked up all kinds of solutions and none have worked. Any advice?

Having some issues to send mails using ssmtp

Actually using a raspberrypi 3 b

/etc*ssmtp/ssmtp.conf

root=gmail_user@gmail.com mailhub=smtp-gmail.com:587  rewriteDomain=gmail.com  hostname=raspberrypi  FromLineOverride=YES  UseSTARTTLS=YES  AuthUser=gmail_user AuthPass=PASSWD 

/etc/ssmtp/revaliases

root:gmail_user@gmail.com:smtp.gmail.com:587 pi:gmail_user@gmail.com:smtp.gmail.com:587 

trying to send a mail

root@raspberrypi:~# echo "hola" | ssmtp gmail_user@gmail.com -v [<-] 220 smtp.gmail.com ESMTP z8sm3685108wru.13 - gsmtp [->] EHLO raspberrypi [<-] 250 SMTPUTF8 [->] STARTTLS [<-] 220 2.0.0 Ready to start TLS [->] EHLO raspberrypi [<-] ssmtp:  (raspberrypi) 

noticed that when i have the user not configurated on /etc/ssmtp/revaliases the output changes

root@raspberrypi:~# echo "hola" | ssmtp gmail_user@gmail.com -v [<-] 220 and/or bulk e-mail. [->] EHLO raspberrypi [<-] 250 HELP [->] STARTTLS [<-] 220 TLS go ahead [->] EHLO raspberrypi [<-] 250 HELP [->] AUTH LOGIN [<-] 334 VXNlcm5hbWU6 [->] ZmlsdGVyLnNydg== [<-] 334 UGFzc3dvcmQ6 [<-] 535 Incorrect authentication data ssmtp: Authorization failed (535 Incorrect authentication data) 

hostname

root@raspberrypi:~# hostname raspberrypi 

ping to google and the DNS servers that im using

root@raspberrypi:~# ping 8.8.8.8 PING 8.8.8.8 (8.8.8.8) 56(84) bytes of data. 64 bytes from 8.8.8.8: icmp_seq=1 ttl=54 time=13.1 ms ^C --- 8.8.8.8 ping statistics --- 1 packets transmitted, 1 received, 0% packet loss, time 0ms rtt min/avg/max/mdev = 13.134/13.134/13.134/0.000 ms root@raspberrypi:~# cat /etc/resolv.conf # Generated by resolvconf nameserver 8.8.8.8 nameserver 8.8.4.4 

also the gmail account have the thing to let less secure aplications use the account

also2, to make sure the name and password where correct, used coppy paste to google chroome ( using ssh so i can copy paste things )

also3, i have a debian server wich works well, also trying to coppy paste all the configuration and change the names from users and hostname but it didn’t worked

(sry if it have some misspellings )

ssmtp, mailutils and GMail how to set username?

Ubuntu 18.04, ssmtp insstalled, mailutils installed and everything works, can send through gmail. My problem is that the messages when received appear to be from “Root (my-real-email@gmail.com)” I am trying to change “root” to a name that wont set off my spam filters at work, which “root” seems to do.

How do I set the username so it appears in the outgoing message as something other than “Root”?

SSMTP on Ubuntu 18.10 server stopped sending email through GMail

I use SSMTP on many of our servers. As of June 6th 2019 I can no longer get SSMTP on any of my ubuntu servers to send email. I have some raspberry pies using the same scripts and they send just fine. On site and offsite using different Google domain names stopped sending, so its not tied to one specific Google apps domain. Nor is it tied to a specific network. All systems are running 18.10. Other things using this same account, send fine, through Ubuntu. PHP mailings for example.

It also does not matter what user I try to use within each Google domain. I can use SSMTP with a yahoo user and that sends from Ubuntu.

When I do ssmtp with -v on a linux box I see:

[<-] 220 smtp.gmail.com ESMTP b6sm3003334iok.71 – gsmtp [->] EHLO munki.xxxxx.com [<-] 250 SMTPUTF8 [->] STARTTLS [<-] 220 2.0.0 Ready to start TLS [->] EHLO munki.xxxxx.com [<-] ssmtp: (munki.xxxxx.com)

When I do the same on a pi I see:

[<-] 220 smtp.gmail.com ESMTP w23sm3846674iod.12 – gsmtp [->] EHLO upsd-c03.xxxxx.com [<-] 250 SMTPUTF8 [->] STARTTLS [<-] 220 2.0.0 Ready to start TLS [->] EHLO upsd-c03.xxxxx.com [<-] 250 SMTPUTF8 [->] AUTH LOGIN [<-] 334 Vjjl;hbWU6 [->] bmFnaW9zQG5XJzLm9yZw== [<-] 334 UGFzc3dvcmQ6 [<-] 235 2.7.0 Accepted [->] MAIL FROM: [<-] 250 2.1.0 OK w23sm38674iod.12 – gsmtp [->] RCPT TO: [<-] 250 2.1.5 OK w23sm38674iod.12 – gsmtp [->] DATA [<-] 354 Go ahead w23sm3874iod.12 – gsmtp [->] Received: by upsd-c03.xxxxx.com (sSMTP sendmail emulation); Fri, 14 Jun 2019 16:59:33 -0500 [->] From: “root” [->] Date: Fri, 14 Jun 2019 16:59:33 -0500 [->] test [->] [->] . [<-] 250 2.0.0 OK 1560549575 w23sm3846iod.12 – gsmtp [->] QUIT [<-] 221 2.0.0 closing connection w23sm3846iod.12 – gsmtp

Just wondering if anyone else using Google to send email with SSMTP has seen the same behavior? I haven’t tested an 18.04 or 19.04.

Thank you!!

Jim