Cannot send an Email out of my Domain

as @cketti showed in https://github.com/thundernest/k-9/issues/6578#issuecomment-1383051785 your message is getting delivered to your outbound relay mail server. why it isn’t reaching your recipient is something you’ll have to take up with your mail server admins. you should, at minimum, be getting a rejection if they (or the recipient’s server) is rejecting the message. you can ask your admins to look at their mail logs for the id that they assign the message on receipt from K9 – e.g., 250 OK id=1pGqpF-0038V7-BS in the dialog from your log.

perhaps related, there is an issue with your rDNS/PTR record. ideally 143.95.226.52 should point back to southcomm.net. instead it is pointing to ip-143-95-226-52.iplocal, which is basically bogus. whether your recipients’ sites reject mail because of this or not is a configuration decision on their side. regardless, if they do your server should be returning the error to you.

additionally, your 143.95.226.52 ipnumber is showing up on a couple of block lists. they weren’t major ones in my view, but the recipient hosts could be using them and handling your mail accordingly.

so, the first question (of your mail server admins) is whether your messages are being delivered to your recipients’ machines.

Addtional information: I have created a gmail email for myself just in the cloud for testing purposes.

Please expalin again because I do not understand the following: Why is it the server the problem if:
Samsung Galaxy S22 Ultra with outlook works ok.
Samsung Galaxy S22 Ultra with Edison Mail works ok.
Samsung Galaxy S22 Ultra with K-9 cannot send a message to any other domain. customers, gmail, etc

All the above have the same IMAP incomming and Outgoing settings.

Also my other company iPhones, , laptop, Desktop PC’s running Thunderbird have no issues

All the things you said are great ideas. I am my own arvixe email server admin. I can check a log or header, but sure looks likes only a K-9 client problem?

Open for any other ideas?

it’s a server problem because … once the message has been accepted by the mail server (as is shown in your logs) subsequent handling of the message is out of K9’s control. the server may be configured in a way to not like something about the message that K9 delivered to it, but once the server has accepted it the server should report that to you. that the messages appear to be disappearing is a problem, and it’s your mail server admins who can (read must) explain that to you. if they are silently tossing them they are operating the server well out of the range of “best practices”.

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I agree with your previous post. I think you are right on the spot by saying, “the server may be configured in a way to not like something about the message that K9 delivered to it”.

I can ony do 2 things:

  1. Does K-9 support have any suggestions of anything that I can toggle on or off to make this paticular IMAP server “like” and deliver the messages.
  2. or I can open a ticket with arvixe technical support, and have them look at a specific message header or something to see why it is not being delivered.

Going to be tough convincing arvixe tech support to work on th problem if I tell them 1 out out of 6 email client apps does not work with their sever?

I am a rank amater at advanced email admin, but if thier is a message header or someting you would want me to post I will try to provide and inforrmation you need. There are aslo email delivery options in the sever if you give me some things to turn on/off?

if you can check the server’s mail logs, then look for the id on the message that was delivered in the dialog previously discussed: id=1pGqpF-0038V7-BS. trace that all the way through and see what happened to it.

if you can’t check the server logs yourself, ask the system admins where that message went?

K9’s mail handling is very standards compliant. if your system’s admins are deviating from the standards it isn’t for K9 developers to try to guess what these deviations are and to make non-standards compliant changes to K9 to match up with whatever your admins have done. there are standards for a reason.

The same thing is happening on my S22ultra for the last week or so. As long as I’m sending within my ISP’s domain (bluehost.com) it works fine, but not to gmail, AT&T, etc. I can also send emails from several other mail client apps, but emails from K9 just disappear. They say they’re sent, but they don’t arrive.
I went to second level, server support with bluehost.com and they assured me that everything is fine on their end and tested several Windows mail clients to prove it.
I have removed the mail account in K9 and reinstated it but it didn’t help.

Thanks,

jbf

Arvixie, Bluehost, and Hostgator are all EIG brands. Hostgator has been confirmed to accept email from K-9 and silently discard it. I would expect all EIG servers to have the same configuration issue.

Yes I had the same problem. My webhosting company for my domain in the cloud is arvixe, and it is intersting to hear that you are having the same problem. Nothing personal against K-9 technical support, but, K-9 tech support responses are not satisfactory. For example: The strict compliance to standards answer I understand. My response is that since Thunderbird 102.6.1 (64 bit) works fine then K-9 needs to have the standards compliance degree of Thunderbird. (and all the other S22 android apps that work. I love Thunderbird and really want K-9 to work. My solution for the time being is to use Edison Mail since I run a business and cannot be down for another week.

I think that seeing K9’s standards compliance as the problem is looking at things the wrong way around. K9 is delivering the mail to your MSP’s server in a standards-compliant manner. In the case of your earlier logs, your logs have shown that your server has accepted the message. Having accepted the message, what your server should be doing is either delivering it to your non-local recipient or returning a bounce/reject to you.

That your MSP’s server is not doing that, and the mail seems to “disappears” (after the server has accepted it), is the [standards compliance] issue. If there’s a problem with the mail that K9 is generating your MSP’s server should reject (or bounce) it.

Once a message has been accepted by your server (and not rejected or bounced) it is out of K9’s hands and there is nothing further that K9 can do - K9 can only assume that your server is handling/delivering it. If your server rejected or bounced it then there would be something to go on, but your server silently dropping it is way off standards compliance and “best practices”.

As indicated previously, log the delivery handling of a message from K9 to your MSP’s server (as you did earlier). If it is successful, at the end your server gives an id, e.g., id=1pGqpF-0038V7-BS. If the message isn’t delivered to the recipient, then ask your server admins to trace that id in their mail logs. With the detailed logging information it will then be possible to discuss what the issue is who can fix what.

And a first step might be that rather than dropping them silently, your MSP’s server can start by rejecting or bouncing messages that it’s not willing to deliver, as is the standard.

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I agree with your statements about standards, but the fact remains that when I send mail with other apps, including Samsung’s default app, it works.

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If, as was shown in @Shar-Pei’s logs, the message is accepted by the MSP’s server and it then “disappears” there is nothing that can be done on the K9 side until the reason the messages are dropped is identified. an even marginally compliant server will either reject a message (from an authenticated user) that it doesn’t plan on delivering or will send back a bounce. lacking any information on why the MSP’s server is dropping the messages there is really nothing that can be done on the K9 side.

so, if you have messages that aren’t being delivered to your intended recipients, start by logging the “send” exchange between K9 and your MSP’s server (see @cketti’s post above in this item for information on logging). if that log shows the message being accepted by the server, then ask your server’s admins to provide the reason (logging detail included) that the message has disappeared. many server’s provide an id on the final “250” on a successful exchange. if yours does, provide that to your server’s admins as that will help them to do the trace.

Hey, I found this thread when looking for a solution to my problem.

I’m customer of DomainFactory (df.eu) and using their mail server to send mails, but I’m using an address of a different domain as identity. When using Thunderbird on Windows, mails to Gmail are working properly. But when I try with K9 from my Android phone, they get rejected.

So even if K9 is very standards compliant, there must be a missing piece of the puzzle.

Who is rejecting the messages, and what - precisely - is the error message you are getting?

Gmail is picky, and getting more so, on how the sending domain/server is identified. You have to have at least an SPF record in the FQDN’s dns allowing the sending/outgoing server to send for it.

If the reject is coming from gmail, providing what you have set for the outgoing server in K-9 and the FQDN (everything to the right of the “@”) on the “From:” on your rejected messages will help in seeing if that’s the issue.

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Here’s what I got in reply. I only changed the gmail address and my domain:

This message was created automatically by mail delivery software.

A message that you sent could not be delivered to one or more of its
recipients. This is a permanent error. The following address(es) failed:

  mygmailaddress@gmail.com
    host gmail-smtp-in.l.google.com [142.250.110.26]
    SMTP error from remote mail server after pipelined end of data:
    550-5.7.26 This mail has been blocked because the sender is unauthenticated.
    550-5.7.26 Gmail requires all senders to authenticate with either SPF or DKIM.
    550-5.7.26
    550-5.7.26  Authentication results:
    550-5.7.26  DKIM = did not pass
    550-5.7.26  SPF [myowndomain.de] with ip: [134.119.228.100] = did not pass
    550-5.7.26
    550-5.7.26  For instructions on setting up authentication, go to
    550 5.7.26  https://support.google.com/mail/answer/81126#authentication 9-20020a05600c028900b0040b385ab364si6932246wmk.182 - gsmtp


Reporting-MTA: dns; smtprelay07.ispgateway.de

Action: failed
Final-Recipient: rfc822;mygmailaddress@gmail.com
Status: 5.0.0
Remote-MTA: dns; gmail-smtp-in.l.google.com
Diagnostic-Code: smtp; 550-5.7.26 This mail has been blocked because the sender is unauthenticated.
 550-5.7.26 Gmail requires all senders to authenticate with either SPF or DKIM.
 550-5.7.26
 550-5.7.26  Authentication results:
 550-5.7.26  DKIM = did not pass
 550-5.7.26  SPF [myowndomain.de] with ip: [134.119.228.100] = did not pass
 550-5.7.26
 550-5.7.26  For instructions on setting up authentication, go to
 550 5.7.26  https://support.google.com/mail/answer/81126#authentication 9-20020a05600c028900b0040b385ab364si6932246wmk.182 - gsmtp


Return-path: <max@myowndomain.de>
Received: from i6dfa39c6.versanet.de ([109.250.57.198] helo=[127.0.0.1])
	by smtprelay07.ispgateway.de with esmtpsa  (TLS1.2) tls TLS_ECDHE_RSA_WITH_AES_128_GCM_SHA256
	(Exim 4.96.1)
	(envelope-from <max@myowndomain.de>)
	id 1rDIG4-00009O-0P
	for mygmailaddress@gmail.com;
	Wed, 13 Dec 2023 06:58:12 +0100
Date: Wed, 13 Dec 2023 06:58:12 +0100
From: Max Wa <max@myowndomain.de>
To: mygmailaddress@gmail.com
Subject: neuer test
User-Agent: K-9 Mail for Android
Message-ID: <1736155A-8EFC-403A-8EFC-79C5D5087CA1@myowndomain.de>
MIME-Version: 1.0
Content-Type: multipart/alternative;
 boundary=----MSKVQHHX3008I3GDWGJ42S1ZYE6PFI
Content-Transfer-Encoding: 7bit
X-Df-Sender: bWF4QG5lZ2dpc2NoLW5hZ2dpc2NoLmRl


I also compared the settings from Thunderbird and K9 closely and they all look the same.

When I sent from Thunderbird and have a look at the raw mail headers, it shows this:

Authentication-Results: mx.google.com;
       spf=neutral (google.com: 134.119.228.104 is neither permitted nor denied by best guess record for domain of max@myowndomain.de) smtp.mailfrom=max@myowndomain.de

I’m puzzled. I just saw that from my phone, I sent to mygmailaddress@gmail.com while on TB, I sent to mygmailaddress@gmail.com. When I use @googlemail.com, it also works on K9. It doesn’t look like a K9 issue at all, but I’d be very pleased if you knew what’s happening here.

the dns record for the FQDN that you are sending from (the part to the right of the @ on the From:) needs an SPF or DKIM record with/that covers all the smtp servers for ispgateway.de (or whatever ESP you are using) as authorized to send mail for your FQDN. most ESPs have how-tos giving the details needed for setting this up for their servers.

it’s possible that google hasn’t implemented this check on mail to @googlemail.com for some reason. the specific gmail To: address is irrelevant.

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Similar issue. K-9 Mail 6.603 installed via F-Droid on my new phone. Old phone used a very old version of K9 successfully. I am using a mail service called hostgator with IMAP. On PC I use Thunderbird with SSL/TLS (465), user@domain and password with zero issues. Outgoing emails from K9 do not arrive. They do not immediately appear in ‘Outbox’. I have gotten like 2 failed to send messages, but have sent a lot more test emails. I have been able to enter user@domain and password, selecting either SSL/TLS (465) or STARTTLS (587) and it seems to pass the password check, but no actual email is sent. One theory is that my service originally used user.domainname@providerspecificmachine for outgoing and K9 may have site specific code to fix the outgoing for this domain? Not sure what else it could be. If contacted privately I could set up an account for testing. My domain is psifoo.com, mail server is ‘mail.’ followed by the domain name. Thanks!

Hi. Update. I can send emails within my own domain. I tried that after reading other posts. So, it gets to the server, but is not sent onward. Works fine with T-Bird. Oh. I forgot to say I use normal password only. I tried sending email to my work server and to a gmail account but neither worked.

Welcome @PeteC :wave:

Usually it’s better to create a new topic instead of posting to an old one. But when you post to an old topic, please read all previous posts to check if your question may have been answered already.

In this case you could have found the answer to your problem here:

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My apologies. First time user. Didn’t think it was a hosting issue as it works with other clients, so didn’t search for provider, just ‘cant send’. Thanks for your help. - Pete

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