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Configure email for Outlook.com (or Hotmail.com)

galileo :

Jun 13, 2019

I have had bvckup2 sending email alerts from my first use of the program using an email address which uses my ISP's email system.  Unfortunately, my ISP's system has has always been painfully slow and, today, I "attempted" to re-configure the email alerts to send through my Outlook.com account.  Note my emphasis on "attempted".

I have been unsuccessful in having bvckup2 connect and/or successfully send email alerts through Outlook.com.  I am using configuration parameters that are identical to another email client (which works correctly) that I am using on the same machine.  I apparently am completely missing something with respect to the configuration.

Using a send to address "xxxx@outlook.com" and the delivery method of "Send directly to the target mail server" fails with: "** Failed, STARTTLS is not supported".  Using the other delivery method of "Use the following mail server" with Hostname: smtp-mail.outlook.com; Port: 587; Security: SMTP + STARTTLS; and appropriate username and password does login but, fails with: "** Failed, the server said - 554  5.2.0 STOREDRV.Submission.Exception: SendAsDeniedException.MapiEx...".

Any help in configuring the email alerts to send through Outlook.com would be greatly appreciated.

galileo

Alex Pankratov :

Jun 13, 2019

Failed, the server said - 554  5.2.0 STOREDRV.Submission.Exception: SendAsDeniedException.MapiEx...


That's the relevant bit. It will give you the exact reason their server refused to accept the email. Most likely it will be due to connecting from the residential IP range and _not_ using authentication (no username/password configured).

The general idea for Outlook/Gmail and others is to set up a separate email account with them just for submitting email alerts for delivery, and then having it relayed to your target account.

In other words, if you primary account is abc@outlook, then you will use another account (xyz@outlook) to connect to their servers, but keep To address on alerts set to abc@outlook. Alert emails then will enter Outlook servers though xyz@ and be forwarded to abc@.

Makes sense?

galileo :

Jun 13, 2019

Not really...given that this works for my ISP's email server - and, the configuration for outlook.com works within a mail client.

I did some research and found one interesting comment regarding the "...SendAsDeniedException...".  The comment noted that this particular error message relates to the "sender" not being identified correctly or rather missing completely in the instance being discussed.

Hence, a question or two:  Given the email settings dialog provided in bvckup2, what is being used as the sender's - or rather "sending" (i.e. "From") email address?  Is the sending address being provided to the smtp server?

From what I inferred from the comments that I read, the smtp logon credentials alone were not adequate without a distinct "From" address.

Alex Pankratov :

Jun 14, 2019

Given the email settings dialog provided in bvckup2, what is being used as the sender's - or rather "sending" (i.e. "From") email address?


It defaults to "noreply@bvckup2.com". You can change this in

    Backup Settings > Email Notifications > How to Send, the From field

Click on "More" to see the field.

From what I inferred from the comments that I read, the smtp logon credentials alone were not adequate without a distinct "From" address.


It's a new development then, probably of anti-spam or anti-phishing nature.

PS. I can have a look at a copy of your %LocalAppData%\Bvckup2\bvckup2-smtp.log if you'd like. Here or via email.

galileo :

Jun 14, 2019

THAT WORKS!  Changing the "From" field entry from the default  "noreply@bvckup2.com" to my email address "***@outlook.com" results in successfully sending the email alert to the desired email account -  i.e. effectively sending the email to myself at outlook.com given that the "Send to" field now matches the "From" field.

Apparently the use of "noreply@bvckup2.com" is the issue, at least for outlook.com.  Anti-spam or anti-phishing trapping may well be what is going on at the receiving end.  Just out of curiosity...is "noreply@bvckup2.com" a valid email address on your end?

Regardless...once again, Thanks Alex.

Alex Pankratov :

Jun 17, 2019

OK, excellent. No, this address is not valid on our end. It bounces.

galileo :

Jun 18, 2019

Apparently that is the reason that some email services reject that address as a valid "From" address.  Hence, the issue with outlook.com.

Interestingly there is a trivial issue with using a valid sending address - not a bvckup2 issue.  Two email confirmations will appear in one's email client:  an email in the "Sent" items folder and another in the "Inbox".  Understandable, in that a real sending address is being used...but annoying nonetheless.

btw:  Congrats on version 80 and your 5 year anniversary!

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