Rejected emails

[Adrian]

I've had three attempts at sending an email to a recipeint (and cc'd to
another), in each case the outcome appears to be the same.

I'm using Turnpike with Stunnel to reach my mail host (emails to other
addressees are getting through OK).

Your message could not be delivered to the following recipients
addressee@domain
Talking to [127.0.0.1] on Wed, 15 Sep 2021 22:53:24 +0100
>>> DATA
<<< 551 5.7.1 Not authorised to send from this header address

cc_addressee@domain
Talking to [127.0.0.1] on Wed, 15 Sep 2021 22:53:24 +0100
>>> DATA
<<< 551 5.7.1 Not authorised to send from this header address

Reporting-MTA: dns; ffoil.org.uk

Final-Recipient: rfc822; addressee@domain
Action: failed
Status: 5.0.0
Remote-MTA: dns; [127.0.0.1]
Diagnostic-Code: smtp; 551 5.7.1 Not authorised to send from this header
address
Last-Attempt-Date: Wed, 15 Sep 2021 22:53:24 +0100

Final-Recipient: rfc822; cc_addressee@domain
Action: failed
Status: 5.0.0
Remote-MTA: dns; [127.0.0.1]
Diagnostic-Code: smtp; 551 5.7.1 Not authorised to send from this header
address
Last-Attempt-Date: Wed, 15 Sep 2021 22:53:24 +0100

I've tried looking up the error codes, but I'm having problems
understanding how it relates to my problem.

Any suggestions on where the problem lies welcome.

Adrian
--
To Reply :
replace "bulleid" with "adrian" - all mail to bulleid is rejected
Sorry for the rigmarole, If I want spam, I'll go to the shops
Every time someone says "I don't believe in trolls", another one dies.

[John Hall]

In message <yJlgrSTp...@ku.gro.lloiff>, Adrian
<bul...@ku.gro.lioff> writes

>I've had three attempts at sending an email to a recipeint (and cc'd to
>another), in each case the outcome appears to be the same.
>
>I'm using Turnpike with Stunnel to reach my mail host (emails to other
>addressees are getting through OK).
>
>Your message could not be delivered to the following recipients
>addressee@domain
> Talking to [127.0.0.1] on Wed, 15 Sep 2021 22:53:24 +0100
> >>> DATA
> <<< 551 5.7.1 Not authorised to send from this header address

<snip>

It looks as though the recipients' email server may have a rule to
reject email coming from 127.0.0.1, which of course is the "dummy" DNS
that you use with Stunnel as a "pass-through". I wonder if it would also
reject 127.0.0.2 - always assuming that using that would be valid.

What happens if you send separate emails to the two addressees rather
than using CC?

Could you send me a test email to my Reply-To address so that I can look
at its headers? Perhaps that might shed some light. Could you also post
here your Stunnel config file?
--
John Hall
"Home is heaven and orgies are vile,
But you *need* an orgy, once in a while."
Ogden Nash (1902-1971)

[Mark Undrill]

My guess would be that you are falling foul of Sender Policy Framework
(SPF). This is causing the SMTP server of some of your correspondent(s)
to reject your e-mail. You will need to add appropriate SPF records for
ffoil.org.uk.

Mark

[Adrian]

In message <jPhpyHBYTwQhFwbj@jhall_nospamxx.co.uk>, John Hall
<john_...@jhall.co.uk> writes

>In message <yJlgrSTp...@ku.gro.lloiff>, Adrian
><bul...@ku.gro.lioff> writes
>>I've had three attempts at sending an email to a recipeint (and cc'd
>>to another), in each case the outcome appears to be the same.
>>
>>I'm using Turnpike with Stunnel to reach my mail host (emails to other
>>addressees are getting through OK).
>>
>>Your message could not be delivered to the following recipients
>>addressee@domain
>> Talking to [127.0.0.1] on Wed, 15 Sep 2021 22:53:24 +0100
>> >>> DATA
>> <<< 551 5.7.1 Not authorised to send from this header address
><snip>
>
>It looks as though the recipients' email server may have a rule to
>reject email coming from 127.0.0.1, which of course is the "dummy" DNS
>that you use with Stunnel as a "pass-through". I wonder if it would
>also reject 127.0.0.2 - always assuming that using that would be valid.
>

Thanks.

Possible, but this is the first time I've run into this particular
problem. Not sure how I'd change the Stunnel IP address. I can
understand why companies may tighten up their incoming filters.

>What happens if you send separate emails to the two addressees rather
>than using CC?
>

I get the same outcome. Both recipients are in the same company (and
hence the same domain).

>Could you send me a test email to my Reply-To address so that I can
>look at its headers?

An email will be with you in a moment or two.

>Perhaps that might shed some light. Could you also post here your
>Stunnel config file?

Ignoring the lines that start with a ";" or a "#"

[pop3s]
client = yes
accept = 127.0.0.1:110
connect = mail.messagingengine.com:995

[ssmtp]
client = yes
accept = 127.0.0.1:25
connect = mail.messagingengine.com:465

[Adrian]

In message <shv0q2$4c7$1...@dont-email.me>, Mark Undrill
<sp...@invalid.invalid> writes

>My guess would be that you are falling foul of Sender Policy Framework
>(SPF). This is causing the SMTP server of some of your correspondent(s)
>to reject your e-mail. You will need to add appropriate SPF records for
>ffoil.org.uk.
>

Thanks, how do I do that with Turnpike ?

[Jim Crowther]

In demon.ip.support.turnpike, on Thu, 16 Sep 2021 19:29:40, Adrian
wrote:

>In message <shv0q2$4c7$1...@dont-email.me>, Mark Undrill
><sp...@invalid.invalid> writes
>>My guess would be that you are falling foul of Sender Policy Framework
>>(SPF). This is causing the SMTP server of some of your
>>correspondent(s) to reject your e-mail. You will need to add
>>appropriate SPF records for ffoil.org.uk.
>>
>
>Thanks, how do I do that with Turnpike ?

You can't - you'll have to alter your DNS settings with Fasthost, or et
them to do it for you.

--
Jim Crowther

[Adrian]

In message <HjIrxnCk...@nospam.at.my.choice.of.UID.invalid>, Jim
Crowther <Don't_bo...@blackhole.do-not-spam.me.uk> writes

Fasthost or Fastmail ?

The former holds my MX records (is that the right terminology), but the
latter handles my emails.

[John Hall]

In message <r+PARpDW...@ku.gro.lloiff>, Adrian
<bul...@ku.gro.lioff> writes

>In message <jPhpyHBYTwQhFwbj@jhall_nospamxx.co.uk>, John Hall
><john_...@jhall.co.uk> writes

<snip>

>>ould you also post here your Stunnel config file?
>
>Ignoring the lines that start with a ";" or a "#"
>
>[pop3s]
>client = yes
>accept = 127.0.0.1:110
>connect = mail.messagingengine.com:995
>
>[ssmtp]
>client = yes
>accept = 127.0.0.1:25
>connect = mail.messagingengine.com:465
>
>Adrian

Mine is very similar. I also have the additional lines

verifyChain = yes
CAfile = ca-certs.pem
checkHost = mail.jhall.co.uk
OCSPaia = yes

in both the SMTP and POP3 sections.

but I don't know if they really make any difference. (My ISP has
cunningly set things up so that mail.jhall.co.uk actually resolves to
their mail server, in case that's confusing.) I don't really understand
what the lines do, but you could try adding them (appropriately changing
the checkHost one) and see if it helps.

[Adrian]

In message <a0VNcsDjo6QhFwef@jhall_nospamxx.co.uk>, John Hall
<john_...@jhall.co.uk> writes

>Mine is very similar. I also have the additional lines
>
>verifyChain = yes
>CAfile = ca-certs.pem
>checkHost = mail.jhall.co.uk
>OCSPaia = yes
>
>in both the SMTP and POP3 sections.
>
>but I don't know if they really make any difference. (My ISP has
>cunningly set things up so that mail.jhall.co.uk actually resolves to
>their mail server, in case that's confusing.) I don't really understand
>what the lines do, but you could try adding them (appropriately
>changing the checkHost one) and see if it helps.

Thanks.

That makes a difference, now it doesn't work at all :-(

From the Stunnel log (subsequent timestamps removed for brevity) :

2021.09.16 23:11:47 LOG5[29]: Service [ssmtp] accepted connection from
127.0.0.1:49928
LOG5[29]: s_connect: connected 66.111.4.52:465
LOG5[29]: Service [ssmtp] connected remote server from 10.0.2.15:49929
LOG5[29]: OCSP: Connecting the AIA responder "http://ocsp.digicert.com"
LOG5[29]: s_connect: connected 93.184.220.29:80
LOG5[29]: OCSP: Certificate accepted
LOG4[29]: CERT: Subject checks failed
LOG4[29]: Rejected by CERT at depth=0: C=AU, ST=Victoria, L=Melbourne,
O=FastMail Pty Ltd, CN=*.messagingengine.com
LOG3[29]: SSL_connect: 14090086: error:14090086:SSL
routines:ssl3_get_server_certificate:certificate verify failed
LOG5[29]: Connection reset: 0 byte(s) sent to TLS, 0 byte(s) sent to
socket

[Mark Undrill]

On 16/09/2021 20:59, Adrian wrote:
> In message <HjIrxnCk...@nospam.at.my.choice.of.UID.invalid>, Jim
> Crowther <Don't_bo...@blackhole.do-not-spam.me.uk> writes
>> In demon.ip.support.turnpike, on Thu, 16 Sep 2021 19:29:40, Adrian
>> wrote:
>>
>>> In message <shv0q2$4c7$1...@dont-email.me>, Mark Undrill
>>> <sp...@invalid.invalid> writes
>>>> My guess would be that you are falling foul of Sender Policy
>>>> Framework (SPF). This is causing the SMTP server of some of your
>>>> correspondent(s) to reject your e-mail. You will need to add
>>>> appropriate SPF records for ffoil.org.uk.
>>>>
>>>
>>> Thanks, how do I do that with Turnpike ?
>>
>> You can't - you'll have to alter your DNS settings with Fasthost, or et
>> them to do it for you.
>>
>
> Fasthost or Fastmail ?
>
> The former holds my MX records (is that the right terminology), but the
> latter handles my emails.
>
> Adrian
>

Fasthost. It's your Mail eXchange (MX) records that will need updating.
Basically you require an SPF record that says "It's OK for mail from
ffoil.org.uk to be sent through messagingengine.com". Hopefully Fasthost
support will be able to assist.

I think the syntax would be something like a TXT record with a value of:

v=spf1 ptr:messagingengine.com

but don't take that as gospel.

Mark

[John Hall]

In message <ufdR5ZUc...@ku.gro.lloiff>, Adrian
<bul...@ku.gro.lioff> writes

That's interesting. I'm groping in the dark here, but I wonder if it's
saying that messagingengine.com doesn't have a certificate that it ought
to have (and which you have now asked it to check for)? In which case,
maybe the email server of the people you are unable to email is also
checking for that certificate and that's why you can't email them,
rather than being anything to do with TP or Stunnel?

A way to test that hypothesis would be to set up a (free) gmail account,
and use it to try emailing them again (still using TP/Stunnel). It would
be a bit of a pain to do that though as, understandably, you can only
have one outgoing email server configured in TP at any one time.

Alternatively, you could give their email addresses to another
TP/Stunnel user (such as myself) and ask them to try emailing them to
see what happens. But if they did receive those emails it might come as
a bit of a shock to them to receive an email from someone they didn't
know from out of the blue.

A final thought. Does your email provider give you the option of
webmail? If so, you could try using that to email them. If that failed
to work, it would confirm that the fault lies with your email provider.

[John Hall]

In message <6rb17bAd1FRhFwDC@jhall_nospamxx.co.uk>, John Hall
<john_...@jhall.co.uk> writes

>I'm groping in the dark here, but I wonder if it's saying that
>messagingengine.com doesn't have a certificate that it ought to have
>(and which you have now asked it to check for)? In which case, maybe
>the email server of the people you are unable to email is also checking
>for that certificate and that's why you can't email them, rather than
>being anything to do with TP or Stunnel?

I suppose that would tie in with the SPF issue that Mark has identified.
As an aside, one would have hoped that when you set up your email
account a competent email provider would have automatically set up the
necessary SPF record.

[Adrian]

In message <si1m6v$t02$1...@dont-email.me>, Mark Undrill
<sp...@invalid.invalid> writes

>Fasthost. It's your Mail eXchange (MX) records that will need updating.
>Basically you require an SPF record that says "It's OK for mail from
>ffoil.org.uk to be sent through messagingengine.com". Hopefully
>Fasthost support will be able to assist.
>
>I think the syntax would be something like a TXT record with a value of:
>
>v=spf1 ptr:messagingengine.com
>
>but don't take that as gospel.
>

Thanks. I've never had to deal with Fasthosts in person (so to speak),
so I don't know how easy that would be to do, and I'm always wary of
doing something that will badly break things.

I have a recollection of setting up the mx records (an online form I
think) something like 9 years ago, when I set up the Fastmail account,
but since then I've only had to interact with them for payments.

[Adrian]

In message <6rb17bAd1FRhFwDC@jhall_nospamxx.co.uk>, John Hall
<john_...@jhall.co.uk> writes

>That's interesting. I'm groping in the dark here, but I wonder if it's
>saying that messagingengine.com doesn't have a certificate that it
>ought to have (and which you have now asked it to check for)? In which
>case, maybe the email server of the people you are unable to email is
>also checking for that certificate and that's why you can't email them,
>rather than being anything to do with TP or Stunnel?
>

Ah, not just me doing the groping in the dark then ;-)

>A way to test that hypothesis would be to set up a (free) gmail
>account, and use it to try emailing them again (still using
>TP/Stunnel). It would be a bit of a pain to do that though as,
>understandably, you can only have one outgoing email server configured
>in TP at any one time.
>

Something that I could try over the weekend. I've got a couple of Gmail
accounts so I might be able to do something with that.

>Alternatively, you could give their email addresses to another
>TP/Stunnel user (such as myself) and ask them to try emailing them to
>see what happens. But if they did receive those emails it might come as
>a bit of a shock to them to receive an email from someone they didn't
>know from out of the blue.
>

That's something I'd rather avoid doing if I can.

>A final thought. Does your email provider give you the option of
>webmail? If so, you could try using that to email them. If that failed
>to work, it would confirm that the fault lies with your email provider.

I think so. I can certainly read stuff whilst it is still on their
server, but I've never had a need to try sending. Again, something to
play with over the weekend.

Thanks again.

[Adrian]

In message <pHqEYGDj...@ku.gro.lloiff>, Adrian
<bul...@ku.gro.lioff> writes

>>A final thought. Does your email provider give you the option of
>>webmail? If so, you could try using that to email them. If that failed

>>work, it would confirm that the fault lies with your email provider.
>
>I think so. I can certainly read stuff whilst it is still on their
>server, but I've never had a need to try sending. Again, something to
>play with over the weekend.
>

Progress Report.

I've tried this approach (a bit of messing about, but I've now got it
configured).
I've sent an email (addressee and cc), with a bcc back to me, and I've
had the bcc, but, so far, no sign of a bounce/rejection.

As the email is a business email, I wouldn't expect a reply until
Monday, so it will take a bit longer before I find out if it got
through.

[Adrian]

In message <Dccg0ANJ...@ku.gro.lloiff>, Adrian
<bul...@ku.gro.lioff> writes

>In message <pHqEYGDj...@ku.gro.lloiff>, Adrian
><bul...@ku.gro.lioff> writes
>>>A final thought. Does your email provider give you the option of
>>>webmail? If so, you could try using that to email them. If that
>>>failed work, it would confirm that the fault lies with your email provider.
>>
>>I think so. I can certainly read stuff whilst it is still on their
>>server, but I've never had a need to try sending. Again, something to
>>play with over the weekend.
>>
>
>Progress Report.
>
>I've tried this approach (a bit of messing about, but I've now got it
>configured).
>I've sent an email (addressee and cc), with a bcc back to me, and I've
>had the bcc, but, so far, no sign of a bounce/rejection.
>
>As the email is a business email, I wouldn't expect a reply until
>Monday, so it will take a bit longer before I find out if it got
>through.
>

Further progress report.

I had a phone call from one of the recipients this morning, wanting to
discuss my email. So it seems that when sent from my Fastmail's website
it gets through, but not when sent from Turnpike. I'd prefer to not
pester them by sending test emails by other routes.

[Cody H]

I think I am running into the same issue you are and the issue at fault is Fastmail's sending identity configuration. I am using ssmtp to send myself automated emails from one of my servers to report health issues. My configuration was working well with a Fastmail account for a long time, but some time in September 2021 my logs started showing these errors:

551 5.7.1 Not authorised to send from this header address

Fastmail support told me to add a "sending identity" through their web ui that matches the email address I am sending my automated mails from:

>As part of our measures to prevent email spoofing through Fastmail, we have made some recent changes requiring that mail be sent from an email address with a corresponding sending identity or a validated external address.
>
>Hence, if you would like to send out emails using this address, please add <redacted> as a sending Identity on the Settings → Sending Identities screen.

This link took me straight to the "Sending Identities" page: https://www.fastmail.com/settings/identities?u=9f0b4140

After adding the address I was able to successfully send a test email from my server with ssmtp.

[Adrian]

In message <9d45fed5-84f5-4239...@googlegroups.com>,
Cody H <mol...@gmail.com> writes

>I think I am running into the same issue you are and the issue at fault
>is Fastmail's sending identity configuration. I am using ssmtp to send
>myself automated emails from one of my servers to report health issues.
>My configuration was working well with a Fastmail account for a long
>time, but some time in September 2021 my logs started showing these errors:
>
>551 5.7.1 Not authorised to send from this header address
>
>Fastmail support told me to add a "sending identity" through their web
>ui that matches the email address I am sending my automated mails from:
>
>>As part of our measures to prevent email spoofing through Fastmail, we
>>have made some recent changes requiring that mail be sent from an
>>email address with a corresponding sending identity or a validated
>>external address.
>>
>>Hence, if you would like to send out emails using this address, please

>>add <redacted> as a sending Identity on the Settings 0 >>Identities screen.

>
>This link took me straight to the "Sending Identities" page:
>https://www.fastmail.com/settings/identities?u=9f0b4140
>
>After adding the address I was able to successfully send a test email
>from my server with ssmtp.

Thanks. I'll have a look at that in detail when I've got a bit of time.
I do send myself emails from my RPis, but they are sent using a Gmail
account, so a tweak on that might be in order.

[Adrian]

In message <9d45fed5-84f5-4239...@googlegroups.com>,
Cody H <mol...@gmail.com> writes

>I think I am running into the same issue you are and the issue at fault
>is Fastmail's sending identity configuration. I am using ssmtp to send
>myself automated emails from one of my servers to report health issues.
>My configuration was working well with a Fastmail account for a long
>time, but some time in September 2021 my logs started showing these errors:
>
>551 5.7.1 Not authorised to send from this header address
>
>Fastmail support told me to add a "sending identity" through their web
>ui that matches the email address I am sending my automated mails from:
>
>>As part of our measures to prevent email spoofing through Fastmail, we
>>have made some recent changes requiring that mail be sent from an
>>email address with a corresponding sending identity or a validated
>>external address.
>>
>>Hence, if you would like to send out emails using this address, please

>>add <redacted> as a sending Identity on the Settings 0 >>Identities screen.

>
>This link took me straight to the "Sending Identities" page:
>https://www.fastmail.com/settings/identities?u=9f0b4140
>
>After adding the address I was able to successfully send a test email
>from my server with ssmtp.

I've had a look at that, and it's still bad news I'm afraid.

In order to contact the addressee, I'd already set up a sending
identity, and sending from the web interface worked. However, I
subsequently tried using the same sending address from Turnpike, and got
an immediate bounce back. I'd already got the two sending addresses
that I use on a regular basis set up in there, and they are working.

I've just tried sending from a different address which hasn't been set
up on Fastmail (to my Gmail account), and that came straight through.

A bit more digging at this end was in order. I had a look at how the
sending address was set up in Turnpike, and it looks as though it wasn't
done properly. Although it was set up with the right name, the
sender/reply to were still set at my old Demon domain (which I stopped
using long before I set up this address. I've tried sending an email,
and I've had an Out Of Office from the recipient, so that appears to be
working. It looks as though when I set up the personality, I only did
half the job with it.

So, it seems that Fastmail (rightly) was objecting to my sending emails
with a Demon domain rather than my domain for the sender/reply to
addresses, the header address that the error message mentions, but
doesn't actually identify.

Thanks to all those who've put forward suggestions on this.

[use reply to]

In message <Kt4zJGLC...@ku.gro.lloiff>, Adrian
<bul...@ku.gro.lioff> writes
>In message <9d45fed5-84f5-4239-a1b4-0ebbce60a258n@googlegroups.c

>om>, Cody H <mol...@gmail.com> writes
>>I think I am running into the same issue you are and the issue at fault is
>>Fastmail's sending identity configuration. I am using ssmtp to send
>>myself automated emails from one of my servers to report health
>>issues. My configuration was working well with a Fastmail account for a
>>long time, but some time in September 2021 my logs started showing
>>these errors:
>>
>>551 5.7.1 Not authorised to send from this header address

[...]

>>After adding the address I was able to successfully send a test email
>>from my server with ssmtp.
>
>I've had a look at that, and it's still bad news I'm afraid.
>
>In order to contact the addressee, I'd already set up a sending identity,
>and sending from the web interface worked. However, I subsequently
>tried using the same sending address from Turnpike, and got an
>immediate bounce back. I'd already got the two sending addresses that I
>use on a regular basis set up in there, and they are working.
[]

I'm also having difficulty setting up Turnpike and Stunnel to send email
via fastmail (no problem with incoming).

I had a few exchanges with Fastmail support in August but they were
unable/unwilling to solve the issue and gave up saying they only support
a few "supported" mail clients such as Thunderbird

At present I am still using Tuffmail for outgoing mail which has worked
absolutely fine with Turnpike/stunnel for years, but unfortunately
tuffmail is shutting down on Jan 1st.

I'd really like to continue using Turnpike past that point, so was
wondering if anyone on this newsgroup is using fastmail for outgoing
mail with TP/stunnel and has settings which will work for sending email
from multiple domains, or alternatively can recommend a free/cheap 3rd
party service for sending via ssmtp using TP/stunnel which will work

Any help much appreciated

Rob
--
Rob Follett

[Adrian]

In message <1IRFoLHT...@letsf.zen.co.uk>, use reply to
<ne...@letsf.co.uk> writes

>I'm also having difficulty setting up Turnpike and Stunnel to send email
>via fastmail (no problem with incoming).
>
>I had a few exchanges with Fastmail support in August but they were
>unable/unwilling to solve the issue and gave up saying they only support
>a few "supported" mail clients such as Thunderbird
>
>At present I am still using Tuffmail for outgoing mail which has worked
>absolutely fine with Turnpike/stunnel for years, but unfortunately
>tuffmail is shutting down on Jan 1st.
>
>I'd really like to continue using Turnpike past that point, so was
>wondering if anyone on this newsgroup is using fastmail for outgoing
>mail with TP/stunnel and has settings which will work for sending email
>from multiple domains, or alternatively can recommend a free/cheap 3rd
>party service for sending via ssmtp using TP/stunnel which will work
>

I'm only using one domain, so I can't comment on using multiple domains
via Stunnel. Can you post your Stunnel conf file so we can a compare
and contrast ?

[John Hall]

In message <1IRFoLHT...@letsf.zen.co.uk>, use reply to
<ne...@letsf.co.uk> writes

>I'm also having difficulty setting up Turnpike and Stunnel to send
>email via fastmail (no problem with incoming).

Could you post the relevant part of your Stunnel config file here, so
that I can take a look at it. Also what error message do you get? You
presumably have the user name and password correctly set in TP Connect >
Configure > Email transfer in the SMTP section.

<snip>

>
>I'd really like to continue using Turnpike past that point, so was
>wondering if anyone on this newsgroup is using fastmail for outgoing
>mail with TP/stunnel and has settings which will work for sending email
>from multiple domains,
> or alternatively can recommend a free/cheap 3rd party service for
>sending via ssmtp using TP/stunnel which will work

The obvious one is Gmail, which IIRC I've successfully used in the past,
with the following Stunnel settings (which I commented out when I
stopped using Gmail for outbound email - though I still use it as an
alternative for inbound):

;[gmail-smtp]
;client = yes
;accept = 127.0.0.1:25
;connect = smtp.gmail.com:465
;verifyChain = yes
;CAfile = ca-certs.pem
;checkHost = smtp.gmail.com
;OCSPaia = yes
;Google say:
;If you connect using SMTP, you can only send mail to Gmail or Google
Apps users; if you connect using SSL/TLS, you can
;send mail to anyone. If your device or application supports SSL -
connect to smtp.gmail.com on port 465. To connect with ;SSL, you need to
provide a Google username and password for authentication.

You probably only really need the first four lines of that - without the
semi-colons of course.

[John Hall]

A websearch for "fastmail smtp settings" turned up this.

Fastmail.com SMTP Server smtp.fastmail.com
SMTP port 465
SMTP security SSL / TLS
SMTP username Your full email address
SMTP password Your Fastmail.com password

That all looks standard and straightforward. So I'd expect the following
Stunnel settings to work, so long as your email address and Fastmail
password are correctly set in TP Connect:

[fastmail-smtp]

client = yes
accept = 127.0.0.1:25

connect = smtp.fastmail.com:465

I imagine that the email address that you use to log into Fastmail will
have to match the one that you've configured TP to put in the From field
of your emails, at least so far as the domain is concerned and perhaps
totally.

[Adrian]

In message <pWqsNHF5rdbhFwTU@jhall_nospamxx.co.uk>, John Hall
<john_...@jhall.co.uk> writes

>A websearch for "fastmail smtp settings" turned up this.
>
>Fastmail.com SMTP Server smtp.fastmail.com
>SMTP port 465
>SMTP security SSL / TLS
>SMTP username Your full email address
>SMTP password Your Fastmail.com password
>
>That all looks standard and straightforward. So I'd expect the
>following Stunnel settings to work, so long as your email address and
>Fastmail password are correctly set in TP Connect:
>
>[fastmail-smtp]
>client = yes
>accept = 127.0.0.1:25
>connect = smtp.fastmail.com:465
>
>I imagine that the email address that you use to log into Fastmail will
>have to match the one that you've configured TP to put in the From
>field of your emails, at least so far as the domain is concerned and
>perhaps totally.

What I've got in my stunnel.conf is :

[pop3s]
client = yes
# Service Level Options

accept = 127.0.0.1:110
connect = mail.messagingengine.com:995

[ssmtp]

client = yes
accept = 127.0.0.1:25

connect = mail.messagingengine.com:465

[use reply to]

In message <M28llmBjGcbhFwlE@jhall_nospamxx.co.uk>, John Hall
<john_...@jhall.co.uk> writes
[]

>Could you post the relevant part of your Stunnel config file here, so that I
>can take a look at it.

Thanks, John

=======
[ssmtp]
accept = 127.0.0.24:25
connect = smtp.mxes.net:465
;connect = smtp.fastmail.com:465
;connect = smtp.messagingengine.com:465
=======

first connect line is tuffmail which works fine
second and third are both fastmail, neither of which work when activated

>Also what error message do you get? You presumably have the user
>name and password correctly set in TP Connect > Configure > Email
>transfer in the SMTP section.

fastmail username and password set correctly as above, tried sending
from my fastmail address (to avoid complications with sending from other
domains) and get the following error:

========
Tue, 19 Oct 2021 00:12:06 SMTP command rejected while talking to
[127.0.0.24]: AUTH PLAIN
cm9iZkBlbWFpbHBsdXMub3JnAHJvYmZAZW1haWxwbHVzLm9yZwBnTjVkU0BCXmJI
535 5.7.8 Error: authentication failed: authentication failure
Tue, 19 Oct 2021 00:12:06 Mail connection to [127.0.0.24] closed, 0
messages transmitted
========

Tuffmail settings work fine sending from any domain...

Thanks for info re gmail, I'll try that tomorrow

Rob
--
Rob Follett

[use reply to]

In message <pWqsNHF5rdbhFwTU@jhall_nospamxx.co.uk>, John Hall
<john_...@jhall.co.uk> writes

>A websearch for "fastmail smtp settings" turned up this.
>
>Fastmail.com SMTP Server smtp.fastmail.com
>SMTP port 465
>SMTP security SSL / TLS
>SMTP username Your full email address
>SMTP password Your Fastmail.com password
>
>That all looks standard and straightforward. So I'd expect the following
>Stunnel settings to work, so long as your email address and Fastmail
>password are correctly set in TP Connect:

Following my earlier reply, I tried restarting the stunnel service and
then got

=========
Tue, 19 Oct 2021 00:23:41 Starting to send mail to [127.0.0.24]
Tue, 19 Oct 2021 00:23:46 SMTP command rejected while talking to
[127.0.0.24]: AUTH PLAIN
cm9iZkBlbWFpbHBsdXMub3JnAHJvYmZAZW1haWxwbHVzLm9yZwBnTjVkU0BCXmJI
535 5.7.0 Sorry, you need to create an app password to use this
service. See our help for more details
=========

Then created an app password via fastmail and used that instead of
normal fastmail password in connect and it then worked...

==========
Tue, 19 Oct 2021 00:35:55 Starting to send mail to [127.0.0.24]
Tue, 19 Oct 2021 00:35:57 Mail for <***@***> sent to [127.0.0.24]
Tue, 19 Oct 2021 00:35:57 Mail connection to [127.0.0.24] closed, 1
messages transmitted
==========

>I imagine that the email address that you use to log into Fastmail will
>have to match the one that you've configured TP to put in the From field of
>your emails, at least so far as the domain is concerned and perhaps
>totally.

Tried sending from a different email address...

==========
Tue, 19 Oct 2021 00:37:41 Starting to send mail to [127.0.0.24]
Tue, 19 Oct 2021 00:37:42 SMTP command rejected while talking to
[127.0.0.24]: DATA

551 5.7.1 Not authorised to send from this header address

Tue, 19 Oct 2021 00:37:42 Mail connection to [127.0.0.24] closed, 0
messages transmitted
==========

so, yes, fastmail will block sending from other addresses, though it
does allow you to post from other addresses via TP/stunnel if you set
them up as aliases within Fastmail... probably over 20 addresses I post
from, so a pain to set up, though doable.

Many thanks, John, and hope this is also helpful for you Adrian (key
actions seem to be restarting stunnel after changes to config, using app
password set in fastmail for TP, and setting any addresses you want to
send from via TP as aliases within fastmail)

Rob
--
Rob Follett

[John Hall]

In message <8jdMgSPE...@ku.gro.lloiff>, Adrian
<bul...@ku.gro.lioff> writes

I've just found this, which indicates that you need to use port 587
rather than 465 for SMTP:

https://www.serversettings.email/fastmail.co.uk-email-server-settings-imap.php

[Adrian]

In message <U7M90ASn...@letsf.zen.co.uk>, use reply to
<ne...@letsf.co.uk> writes

>so, yes, fastmail will block sending from other addresses, though it
>does allow you to post from other addresses via TP/stunnel if you set
>them up as aliases within Fastmail... probably over 20 addresses I post
>from, so a pain to set up, though doable.
>

Interesting. As I mentioned up thread, I've found that I'm able to send
from Turnpike using an address that isn't set up with Fastmail.

To clarify, Fastmail knows about my domain, and I've got three addresses
set up with Fastmail (e.g. a@domian, b@domain and c@domain), but I've
been able to send emails using d@domain (and others)

If you've got another address that you can send to (e.g. a gmail
account), it might be worth trying it before you set them all up.

[use reply to]

In message <tWF1EqBO...@ku.gro.lloiff>, Adrian
<bul...@ku.gro.lioff> writes
[]

>If you've got another address that you can send to (e.g. a gmail
>account), it might be worth trying it before you set them all up.

[]

Thanks, Adrian, but all now setup and working very well. I do have a
gmail account and pick up mail from it in TP, but prefer to send via
Fastmail (or previously Tuffmail) due to potential privacy issues with
gmail

Rob
--

[Adrian]

In message <2ZuVcEFy...@letsf.zen.co.uk>, use reply to
<ne...@letsf.co.uk> writes

Good to hear that things are working now.

To avoid any confusion, I was suggesting the use of the gmail account
for testing purposes only. (send an email with subject and body of
"Test" via Fastmail to gmail). That ought to be safe, unless you are
worried about exposing your "real" email addresses to gmail.