Outlook.com Moving Addresses From Bcc Field to the TO Field When Email is Sent via Desktop Email Client

Ron:

After receiving your latest reply, I once again tested and sent an email to see if the SMTP Outllook.com server was fixed and would send emails to a Bcc address using a desktop email program with addresses in the TO, Cc, and Bcc fields. The email never gets to the Bcc address.

Your reply to me above on May 30th confirmed what I have been and continue to experience as a problem. If I use a web browser, everything works. If I use a desktop email program using an outgoing SMTP server other than Outlook.com, everything works. If I use a desktop email program using the outgoing SMTP server at Outlook.com (see below), the address in the Bcc field never receives the email.

Here is a quick summary:

1. I am using incoming imap-mail.outlook.com Port 993 and outgoing smtp-mail.outlook.com Port 587 for my Outlook.com server settings in my desktop email program.
2. I am accessing my email via IMAP according to the specifications shown under "Settings/Options/Account/POP and IMAP" on the Outlook Mail web page.
3. I am using the desktop email client program “Postbox” and have tried it using "Thunderbird".

4. Using “Postbox” desktop email program to send an email via the Outlook.com SMTP server. The fields and results were:

• From field used a “Live” email account going through the Outlook.com SMTP server.
• To field had a “Live” email address. The email was received.
• Cc field had a “Yahoo” email address. The email was received.
• Bcc field had a “Gmail” email address. The email was NOT received.

If you need more, please let me know.

I just tested sending emails with an address in To and addresses in Bcc.

All emails were received.

What are you using for the server address?

Is the account setup using pop3 or IMAP?

Ron:

It is now June 23rd. Is MS investigating and trying to resolve these problems, or does MS consider them minor bugs and not working on them?

Here is more insight if it will help anyone.

Problems when using a desktop email client and sending through SMTP server at Outlook.com:

1. When I do not have an email address in the “To” field, do not have an email address in the “Cc” field, do put a single email address or a group list into the Bcc field, and send the email from my “Postbox” email desktop client through my outgoing SMTP server at "Outlook.com", the email goes through "Outlook.com" and "Outlook.com" moves all the email addresses from the “Bcc” field to the “To” field (All my email addresses used to stay in the “Bcc” field as they should until my web account was changed from Outllook.com to Outlook Mail).
2. When I put an email address in the "To" field, another email address in the "Cc" field and two more email addresses in the "Bcc" field, and send the email from my “Postbox” email desktop client through my outgoing SMTP server at "Outlook.com", the result is that the email addresses used in the "To" and "Cc" fields receive emails from me and the email addresses used in the "Bcc" field never receive my emails when I send from my SMTP server at “Outlook.com”.

Notes:

1. My Outlook web page has shown “Outlook Mail” in the top left corner instead of “Outlook.com” for many weeks.
2. I am using incoming imap-mail.outlook.com Port 993 and outgoing smtp-mail.outlook.com Port 587 for my desktop email client server on “Postbox”.
3. I verified all my “Junk” email settings on my Outlook Mail web page.
4. I do not have any “Inbox rules” or “Sweep rules” in my email settings on my Outlook Mail web page.

Testing:

I am reporting a comprehensive set of tests and results using a desktop email client "Postbox", using a desktop email client "Mozilla Thunderbird", a browser mail through “CenturyLink”, a browser mail through “Gmail”, and a browser mail through “Outlook Mail”.

• T1 - Using “Outlook Mail” through the browser to send an email. The fields and results were:
  • From field used a “Live” email account.
  • To field had a “Gmail” email address. The email was received.
  • Cc field had a “Live” email address. The email was received.
  • Bcc field had a “CenturyLink” email address. The email was received.
• T2 - Using “CenturyLink” through the browser to send an email. The fields and results were:
  • From field used a “CenturyLink” email account.
  • To field had a “Live” email address. The email was received.
  • Cc field had a “Gmail” email address. The email was received.
  • Bcc field had a “Yahoo” email address. The email was received.
• T3 - Using “Gmail” through the browser to send an email. The fields and results were:
  • From field used a “Gmail” email account.
  • To field had a “CenturyLink” email address. The email was received.
  • Cc field had a “Yahoo” email address. The email was received.
  • Bcc field had a “Live” email address. The email was received.
• T4 - Using “Postbox” desktop email client to send an email. The fields and results were:
  • From field used a “Live” email account going through the Outlook.com SMTP server.
  • To field had a “Live” email address. The email was received.
  • Cc field had a “Yahoo” email address. The email was received.
  • Bcc field had a “Gmail” email address. The email was NOT received.
• T5 - Using “Postbox” desktop email client to send an email. The fields and results were:
  • From field used a “CenturyLink” email account going through the Centurylink.net SMTP server.
  • To field had a “Live” email address. The email was received.
  • Cc field had a “Yahoo” email address. The email was received.
  • Bcc field had a “Gmail” email address. The email was received.
• T6 - Using “Mozilla Thunderbird” desktop email client to send an email. The fields and results were:
  • From field used a “Live” email account going through the Outlook.com SMTP server.
  • To field had a “Yahoo” email address. The email was received.
  • Bcc field had “CenturyLink”, “Gmail”, and “Live” email addresses. The emails were NOT received.
• T7 - Using “Postbox” desktop email client to send an email. The fields and results were:
  • From field used a “Live” email account going through the Outlook.com SMTP server.
  • To field had no email address.
  • Bcc field had “Gmail” email addresses. The email was received but the address was moved from the Bcc field to the “To” field and the address was visible.

Conclusions:

1. Based on all of the above testing, the problems mentioned above seem to be when there is a combination of using a desktop email client to send an email through the “Outlook.com” SMTP server and putting one or more addresses in the Bcc field as shown in the T4, T6, and T7 tests above. The email address in the Bcc field for T4 and T6 never received the email sent to that address. And, the email address in the Bcc field for T7 was moved to the “To” field and subsequently received.
2. When I checked the source data from the sent messages from T4 and T6, the Bcc information and addresses were all striped away and nonexistent. Apparently something done by the Outlook.com SMTP server processing.
3. When I checked the source data from the sent message from T7, the Bcc information and address was blank and the “To” field contained the address. Apparently something done by the Outlook.com SMTP server processing.

Ron:

THANKS!!

I think you figured out the problem. I hope you agree that all email software, including the MS Office 365 server, should send Bcc emails from a desktop client because Bcc is an integral part of the email process, and I ask you to pass your findings to your MS technical support personnel so they can correct the situation.

Again - thanks and please let me know when this will be fixed.