How to check email was delivered to recipient?

[#1]

Hi- first time here.
I sent a v important email to 2 people at same organisation 5 days ago, with Bcc to me and a saved copy in my web mail ''Sent' file but they are pretending they did not receive it.
I accessed the web on my home computer (Mac 0SX: 10-4-11: PPC G5) but I sent the email from the web/remote access for my home Mac Mail account.  New to b-band and Plusnet so not finished adjusting all my settings so at mo I can receive mail to my home mac mail POP3 account but I can't send emails- that's why I logged onto my remote access mail to send.  Hope this is clear.
So- is there a way I can trace the email that I sent from my web/mail account to the 2 recipients addresses and check that they (theoretically) should have received it?  I do not understand how they can deny knowledge of the email while I got my sent copy and there is a copy in my web sent/mail.  Any comments- advice- encouragement v much appreciated.

[#2]

Several possibilities -
1)  Are you absolutely sure the address you sent it to is correct ?
2) Your email might well have been received, BUT got filed in a SPAM folder - or worse deleted.
3)  I have apparently lost emails before because the recipients email provider only provides a very small storage allocation, and my messages were received and then automatically discarded as any new messages took the account over the limit !.

What I have done in the past (albeit on a Windoze PC), is that in my desktop email client (Pegasus mail), there were options to request "DELIVERY NOTIFICATION" and "MESSAGE READ NOTIFICATION".
With these options selected (and assuming the recipients email is not set to ignore the requests), then your outgoing messages can return a status email indicating that your message has been delivered to the target mailbox, and you also get a notification of when (or if) your message has been opened for reading.  It might be worth seeing if your email program has an equivalent function, but do bear in mind that it does rely also on the recipients email system working correctly.
It might also be worth getting your recipient to send you an email you first, then you REPLY to their message, that way you are guaranteed to use their actual email address - not just what they have told you it should be !

[#3]

A long time ago I was advised to turn off "DELIVERY NOTIFICATION" and "MESSAGE READ NOTIFICATION". - as they are a security / spam risk.
Company email systems have had this function turned off and with no ability to turn it on.

[#4]

Proprietary protocols (Outlook and suchlike) or a properly robust open protocol such as X.400 support such receipts, but SMTP was never designed to support delivery or read notifications, so you are dependent on clients and/or end-point mail servers and/or gateways (mail protocol translators) supporting such a mechanism.
Plus of course as mal0z  says, you can usually turn the automatic receipt sending off at the recipeint's end (which is what I do at work)
Worth remembering that internet email is not a guaranteed delivery system; so if it's so important you need an acknowledgement of receipt, send a registered & signed-for letter!

[#5]

You could turn it on if you were one of the users of my corporate network, however, I have my Exchange Server set to only process them for internal mails - they are never sent nor received for external mails.
Just to make you aware that it isn't entirely foolproof.
The only guarantee is to put the mail online in a secure location with tracking for who has read it.
It's probably easier to just post it though unless you were doing it very often, or for lots of people.

[#6]

That reminds me - as already mentioned SMTP email was never designed as a secure communications protocol.
Even the good old Telex with Murray / Baudot code had an answer back mechanism where you could interogate a remote machine and get it's number and code.
BT's Telecom Gold email used X.400 so it did have such a feature.
So maybe BT and other major telco's should promote a decent email system along with International Telecommunication Union.
Maybe they are

[#7]

The installed base of SMTP based systems is just too huge now, there'll only be step change.
There is an additional RFC which describes a protocol for notifications over SMTP but it would need a lot of uptake (and some mechanism for the receipts to pass unscathed through a non-compliant mailserver)  to make it work consistently and well. I have no idea whether it is implemented anywhere yet, I'd be interested to know.
X.400 was a beautiful protocol in it's way but was committe-designed ... it was complicated and expensive to implment. It is probably still used in some mutlinationals and for mail backbones for the bigger mail carriers. Security and other intelligence services certainly used it and I'd be surprised if they did not still.
Improvements in technology probably make it easier to implement these days but I'd guess it's really dead in the water in the 21st century

[#8]

Quote from: purleigh

1)  Are you absolutely sure the address you sent it to is correct ? 2) Your email might well have been received, BUT got filed in a SPAM folder - or worse deleted. 3)  I have apparently lost emails before because the recipients email provider only provides a very small storage allocation, and my messages were received and then automatically discarded as any new messages took the account over the limit !. Quote from: paulh Worth remembering that internet email is not a guaranteed delivery system; so if it's so important you need an acknowledgement of receipt, send a registered & signed-for letter!

Thanks to you all for your feedback/comments.
I am not employed within the same (large) organisation; I had a meeting with them face-to-face out of their office on Monday re complaints I've made about their service/behaviour and they asked me to email them later that day with my availability for a home visit/discussion to take place this last week now gone.  I promised I would email them and as they were 'expecting' my email response, I would not then expect them to have me marked as spam (although they could possibly have done it deliberately to then say - sorry- we didn't get it due to admin mistake).  Also, the email they got before the email in question was only sent the night before and that got there as this was the email they used to 'reply' to me stating they had not had a response from me.
I've sent emails to the recipients addresses for 2 years and there are 2 email addresses I always use to send to them and to receive email (depending on my location) and I've never had any warning or notification of non delivery and I did not in this instance.
I've had 'out of office' responses from them recently when I needed them to respond- although the dates indicate they have not gone yet or should already be back at the office- but that is because they just don't reply if it serves their purpose. As a test I've sent the same message from the same web email to friends and they have all received it and I have checked on my email web server/account- no service problems at the time of sending (wouldn't that have shown up when I sent it or at least since then?).  I'm 99.9% sure they got it but it seems I just can't prove it.  Oh well- I was in the mood for exposing their lies.
Thanks again though.
Helen

[#9]

Print a copy of the email and fax it to them. If they have more than one fax number at their end send the fax to them all.
If you know their manager send the fax to them as well. Your fax machine will confirm the fax has been sent.

[#10]

Hi Santiago.
I don't have a fax (so have not used to send coms previously) but I will keep that in mind about poss faxing in future. However - is this foolproof as my email servers said the emails were sent?
When I have tried to clarify who to communicate to- they usually name someone who is leaving their employ or going on annual leave for 3 weeks (they don't tell me this- I find this out by chance).  They have already recently managed 9 weeks delay by having all 3 people that I was told to respond to suddenly being on indefinite leave/sick/annual leave etc. etc.
Checked today with another complainant correspondent and he has been sending to the same addresses (I triple checked the email addresses) and no problem- but he also only gets a response from them only when it suits them.  Unfortunately the ones I am communicating with are heads of department/directors/chief execs and so the rot goes all the way up and that's one of the reasons why it has been going on so long.
Thanks- Helen

[#11]

sounds like one I have been dealing with since Aug, now nearing completion.  When a fax is sent, you get an immediate return of the ID of the receiving station, time, and ID

[#12]

Thanks for confirming that pierre-pierre.
Helen

[#13]

Yep - the fax protocol includes an initial handshake, and a confirmation at the end that all the data has been sent.
On older/slower machines, you see the paper pause partway through whilst the machine at the other end processes the data and prints it.
Generally there is an option to print the TX (Transmission) report to confirm it was sent.

[#14]

Does their mail server bounce messages to unknown recipients? If so could you add a CC to test.delivery@theirdomain.co.uk, the bounce message would prove that it was delivered to their server as there would be multiple email addresses on the original email but only one rejected in the bounce.

[#15]

Quote from: jelv

Does their mail server bounce messages to unknown recipients? If so could you add a CC to test.delivery@theirdomain.co.uk, the bounce message would prove that it was delivered to their server as there would be multiple email addresses on the original email but only one rejected in the bounce.

Hi jelv
That's an interesting one- can you just clarify a couple of points for me as I really am having to go out of my depths with all this-
I don't know if their mail server bounce messages to unknown recipients- how can I check this? and ...
If I send a Cc to 'test.delivery@theirdomain.co.uk' as you suggest- do you mean that I should replace '@theirdomain.co.uk'  with the address that all the intended recipients share in this organisation (eg) Cc to: testdelivery@verybadcompany.org.uk ...or exactly as you have written it? 
The 'usual suspects' are still not responding to my last 2 emails and I'm drafting another to send and I'd like to include this Cc test when I send it.  Sounds good!
Helen