From Newsgroup: uk.telecom.broadband

My mother is having intermittent problems with Outlook (Office
Professional Plus 2024). Sometimes it claims to have sent an email, and
the message ends up in Outlook's Sent Items mailbox, but the recipient
never receives it. If she sends from the Samsung email app on her phone,
the email gets through OK. Both are connected to the same internet
connection and use the same SMTP server.

The ISP is Plusnet. It happened when their email used their own server relay.force9.net, and it's still happening now her email has been
migrated to Greenly, still using the same server name - the transfer to Greenly was done in such a way that email clients do not need to be reconfigured with Greenly POP and SMTP server addresses.

I'm about to suggest that she copies herself on sent emails to see if
*she* receives the email that she is sending.
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From Newsgroup: uk.telecom.broadband

On 29/12/2025 10:01, NY wrote:

My mother is having intermittent problems with Outlook (Office
Professional Plus 2024). Sometimes it claims to have sent an email, and
the message ends up in Outlook's Sent Items mailbox, but the recipient
never receives it. If she sends from the Samsung email app on her phone,
the email gets through OK. Both are connected to the same internet connection and use the same SMTP server.

The ISP is Plusnet. It happened when their email used their own server relay.force9.net, and it's still happening now her email has been
migrated to Greenly, still using the same server name - the transfer to Greenly was done in such a way that email clients do not need to be reconfigured with Greenly POP and SMTP server addresses.

I'm about to suggest that she copies herself on sent emails to see if
*she* receives the email that she is sending.

OK, so it sounds like some emails are getting delivered and some are
not. Is that correct? Is there any particular pattern to those which are
not - such as being addressed to Hotmail accounts? Sometimes Hotmail in particular decides to blacklist Plusnet addresses for no obvious reason.
Can you ask the would-be recipients to look in their spam/junk folders
in case the emails have gone there rather than to the inbox? I've come
across this sort of thing numerous times.

The problem is almost certainly with the recipients' email provider
rather than with your mother's Outlook setup.
--
Cheers,
Roger
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From Newsgroup: uk.telecom.broadband

On 29/12/2025 19:56, Roger Mills wrote:

On 29/12/2025 10:01, NY wrote:

My mother is having intermittent problems with Outlook (Office
Professional Plus 2024). Sometimes it claims to have sent an email,
and the message ends up in Outlook's Sent Items mailbox, but the
recipient never receives it. If she sends from the Samsung email app
on her phone, the email gets through OK. Both are connected to the
same internet connection and use the same SMTP server.

The ISP is Plusnet. It happened when their email used their own server
relay.force9.net, and it's still happening now her email has been
migrated to Greenly, still using the same server name - the transfer
to Greenly was done in such a way that email clients do not need to be
reconfigured with Greenly POP and SMTP server addresses.

I'm about to suggest that she copies herself on sent emails to see if
*she* receives the email that she is sending.

OK, so it sounds like some emails are getting delivered and some are
not. Is that correct? Is there any particular pattern to those which are
not - such as being addressed to Hotmail accounts? Sometimes Hotmail in particular decides to blacklist Plusnet addresses for no obvious reason.
Can you ask the would-be recipients to look in their spam/junk folders
in case the emails have gone there rather than to the inbox? I've come across this sort of thing numerous times.

The problem is almost certainly with the recipients' email provider
rather than with your mother's Outlook setup.

Ah, I've realised that I forgot to mention one crucial point: in both
cases (Outlook and Samsung) it's from the same address (hers) via the
same SMTP server to the *same* recipient address.

I wonder if it might be significant that her address is x@y.force9.co.uk
and she uses SMTP relay.force9.net. Although I use Plusnet as well, mine
is x@y.plus.com and I use relay.plus.net. Could there be any difference?
I'm not aware of any problems sending from my account to anyone, using
either Windows Live Mail (Win7) or Thunderbird (Win10).
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From Newsgroup: uk.telecom.broadband

NY wrote:
[snip]

Ah, I've realised that I forgot to mention one crucial point: in both
cases (Outlook and Samsung) it's from the same address (hers) via the
same SMTP server to the *same* recipient address.

I wonder if it might be significant that her address is x@y.force9.co.uk
and she uses SMTP relay.force9.net. Although I use Plusnet as well, mine
is x@y.plus.com and I use relay.plus.net. Could there be any difference?
I'm not aware of any problems sending from my account to anyone, using either Windows Live Mail (Win7) or Thunderbird (Win10).

Does both her Outlook and her Samsung use the same SMTP server,
username, password and security settings (SSL, TLS etc?)

We need to establish whether the message is successfully transmitted to
the SMTP server. If she copies messages to you, and you receive them,
that confirms successful transmission.

Messages sent from the ISP's SMTP server to the ultimate recipient might
fail. Sometimes this will be reported back to the sender.

A professional email supplier will be able to monitor the SMTP traffic
to establish whether their server receives the message from Outlook, and whether it is delivered to the recipient's mail server. In principle
Plusnet could provide this monitoring, but trying to find somebody who understands the issue might be a challenge. The name Bob Pullen comes
to mind ...
--
Graham J
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From Newsgroup: uk.telecom.broadband

On 2025/12/29 22:48:27, Graham J wrote:

NY wrote:
[snip]

Ah, I've realised that I forgot to mention one crucial point: in both
cases (Outlook and Samsung) it's from the same address (hers) via the
same SMTP server to the *same* recipient address.

I wonder if it might be significant that her address is x@y.force9.co.uk
and she uses SMTP relay.force9.net. Although I use Plusnet as well, mine
is x@y.plus.com and I use relay.plus.net. Could there be any difference?
I'm not aware of any problems sending from my account to anyone, using
either Windows Live Mail (Win7) or Thunderbird (Win10).

Does both her Outlook and her Samsung use the same SMTP server,
username, password and security settings (SSL, TLS etc?)

We need to establish whether the message is successfully transmitted to
the SMTP server. If she copies messages to you, and you receive them,
that confirms successful transmission.

Messages sent from the ISP's SMTP server to the ultimate recipient might fail. Sometimes this will be reported back to the sender.

A professional email supplier will be able to monitor the SMTP traffic
to establish whether their server receives the message from Outlook, and whether it is delivered to the recipient's mail server. In principle Plusnet could provide this monitoring, but trying to find somebody who understands the issue might be a challenge. The name Bob Pullen comes
to mind ...

Indeed.

Has the problem more or less coincided with the outsourcing to Greenby?
I've had a few wrinkles - mainly, popups (from Thunderbird I think)
saying it can't connect to the server, and occasional prompts to
re-enter my (unchanged) password.

Touch wood, these have settled down in the last day or two. From
experience with problems with PlusNet mail, this might be normal -
things malfunction for a few days (maybe even up to a week or two), then
settle down - with no actual _admission_ (that I'm aware of, anyway)
from PLusNet that anything had been wrong and fixed.

(The last problem I remember having was certain destinations - I think
gmail was one - started bouncing my emails, possibly because I don't use
a PlusNet "From: ". This had been permanent a few _years_ earlier, which
had to be sorted by adding PlusNet's server names [something _different_
from relay.plus.net, by the way] to a line at my hosting provider, so
gmail could ask it "is this person allowed to send via this server". The
more recent recurrence cleared up after a few days, without my having to
do anything; that might have been early teething troubles with the
Greenby outsourcing.)
--
J. P. Gilliver. UMRA: 1960/<1985 MB++G()ALIS-Ch++(p)Ar++T+H+Sh0!:`)DNAf

"Get off my turf!" screamed Pooh, as he shot at Paddington.
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