sending from gmail fails

[ArtZL]

I'm trying to send an email from a gmail account. Don't know why it fails. Any suggestions?

I know my user ID and password are ok because when I put in a bad ID, an error message says its a bad ID or pwd.

MY COMMAND LINE:
mailsend -v -f MyGmailAcct@gmail.com" -t Someone@Somewhere.com -starttls -port 587 -auth -smtp smtp.gmail.com -user MyGmailAcct@gmail.com -pass MyPassword -sub "Testing Art's Email" -disposition inline -attach "body.txt" -log "c:\temp\log.txt"

LOG FILE
17-May-2018 20:18:35.137: mailsend v@(#) mailsend v1.20b
17-May-2018 20:18:35.137: Connecting to smtp.gmail.com:587
17-May-2018 20:18:35.137: Will detect IPv4 or IPv6 automatically
17-May-2018 20:18:36.824: [S] 220 smtp.gmail.com ESMTP 15-v6sm2807902oix.25 - gsmtp
17-May-2018 20:18:36.825: [C] EHLO localhost

17-May-2018 20:18:37.827: [S] 250-smtp.gmail.com at your service, [2600:1702:27c0:42b0:99e:94d1:a4b0:cc67]
17-May-2018 20:18:37.828: [S] 250-SIZE 35882577
17-May-2018 20:18:37.828: [S] 250-8BITMIME
17-May-2018 20:18:37.829: [S] 250-STARTTLS
17-May-2018 20:18:37.830: [S] 250-ENHANCEDSTATUSCODES
17-May-2018 20:18:37.830: [S] 250-PIPELINING
17-May-2018 20:18:37.831: [S] 250-CHUNKING
17-May-2018 20:18:37.831: [S] 250 SMTPUTF8
17-May-2018 20:18:37.831: [C] STARTTLS

17-May-2018 20:18:38.827: [S] 220 2.0.0 Ready to start TLS
17-May-2018 20:18:40.825: [C] EHLO localhost

17-May-2018 20:18:41.823: [S] 250-smtp.gmail.com at your service, [2600:1702:27c0:42b0:99e:94d1:a4b0:cc67]
17-May-2018 20:18:41.824: [S] 250-SIZE 35882577
17-May-2018 20:18:41.824: [S] 250-8BITMIME
17-May-2018 20:18:41.824: [S] 250-AUTH LOGIN PLAIN XOAUTH2 PLAIN-CLIENTTOKEN OAUTHBEARER XOAUTH
17-May-2018 20:18:41.825: [S] 250-ENHANCEDSTATUSCODES
17-May-2018 20:18:41.825: [S] 250-PIPELINING
17-May-2018 20:18:41.825: [S] 250-CHUNKING
17-May-2018 20:18:41.825: [S] 250 SMTPUTF8
17-May-2018 20:18:41.826: Server does not support AUTH CRAM-MD5
17-May-2018 20:18:41.826: Using AUTH LOGIN
17-May-2018 20:18:41.826: [C] AUTH LOGIN

17-May-2018 20:18:42.825: [S] 334 VXNlcm5hbWU6
17-May-2018 20:18:42.826: [C] QXJ0TGllYmVybWFuQGdtYWlsLmNvbQ==

17-May-2018 20:18:43.828: [S] 334 UGFzc3dvcmQ6
17-May-2018 20:18:43.828: [C] QXJ0c0dvb2dsZUFjY3QhMQ==

17-May-2018 20:18:44.826: [S] 534-5.7.14 <https://accounts.google.com/signin/continue?sarp=1&scc=1&plt=AKgnsbuo
17-May-2018 20:18:44.827: Error: AUTH LOGIN failed: '534 5.7.14 <https://accounts.google.com/signin/continue?sarp=1&scc=1&plt=AKgnsbuo'
17-May-2018 20:18:44.827: Could not send mail

[muquit]

Please login to the sender account in gmail and make sure that gmail is not blocking it. gmail does not allow sending mail from any "untrusted" app by default. If this is the case you have to configure gmail to allow it. Also if you are using windows, use double quotes around the sender's password.

Thanks.

[ArtZL]

Yes, you are correct. I have received an email from gmail saying they are blocking emails from this "untrusted" app. My program is used by churches who will be sending emails to their members. Some of those churches use Gmail for handling all of their email (incoming and outgoing). So, each church would have to "lower their shields" to allow untrusted apps. And they won't be willing to do that.

I'm just not sure what to do about this. Probably my only option would be to set up my own gmail account just for this purpose, and have all email from all churches come from this one account. Then use the -rt parameter with the church's actual email address.

[ArtZL]

Thanks for your quick and helpful response. And thank you for the use of your program! Art From: muquit Sent: Thursday, May 17, 2018 8:51 PM To: muquit/mailsend Cc: ArtZL ; Author Subject: Re: [muquit/mailsend] sending from gmail fails (#132) Please login to the sender account in gmail and make sure that gmail is not blocking it. gmail does not allow sending mail from any "untrusted" app by default. If this is the case you have to configure gmail to allow it. Also if you are using windows, use double quotes around the sender's password. Thanks. — You are receiving this because you authored the thread. Reply to this email directly, view it on GitHub, or mute the thread.

[muquit]

gmail allows to generate an app specific password. This password can be used to send email instead of the regular user password. You can try that.

[ArtZL]

I’ve found that most online email services (gmail, yahoo, ...) put limits on the number of emails per day or per hour. For my application, limits are not acceptable. So I have the perfect work-around: I tell my users that email can be sent only from their own smtp account, not an online account. If they don’t have the right kind of account, they can’t do email. I like that solution. It keeps things simple (for me). Thanks, Art From: muquit Sent: Thursday, May 17, 2018 9:56 PM To: muquit/mailsend Cc: ArtZL ; Author Subject: Re: [muquit/mailsend] sending from gmail fails (#132) gmail allows to generate an app specific password. This password can be used to send email instead of the regular user password. You can try that. — You are receiving this because you authored the thread. Reply to this email directly, view it on GitHub, or mute the thread.

[alejandro5042]

In addition,, you may want to look into services like https://sendgrid.com/ with its SMTP service.

[atesin]

don't use "EHLO localhost" envelope

chances are your message (and maybe your account) will be blocked

how it works?? ... you send the mail:

EHLO localhost
blah

• at this point, the mail server reads the HELO/EHLO hostname specified, and tries to resolve the IP address
• then it looks the SRC_ADDR from the tcp/ip packets, from where your message were received, both addresses should match
• if not, the message could be impersonating another sender/domain, the message could be dropped and the account blocked

suggestion: use a public domain that is correcty resolved from outside internet... your own domain, configured, or at least use some free ddns service/subdomain

[muquit]

Did you try the option -domain ?

mailsend -h 
...
-domain    domain     - domain name for SMTP HELO/EHLO
...

Thanks.