The support forum

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!

bvck_it_up :

Feb 12, 2020

Hi guys, I am also struggling with this problem. I have created a new Outlook address for alerts and have changed the From settings as mentioned above, however, I am now getting an error "535 5.7.3 Authentication unsuccessful..."

Contents of %LocalAppData%\Bvckup2 below

Appreciate your help!

2020.02.12 22:20:51.130 (UTC+10) 3 State 3 -> 5
2020.02.12 22:20:51.131 (UTC+10) 3 (dns) Looking up A record for smtp-mail.outlook.com ...
2020.02.12 22:20:51.279 (UTC+10) 3 (dns)   [record of type 5]
2020.02.12 22:20:51.280 (UTC+10) 3 (dns)   [record of type 5]
2020.02.12 22:20:51.280 (UTC+10) 3 (dns)   [record of type 5]
2020.02.12 22:20:51.280 (UTC+10) 3 (dns)   52.98.9.130
2020.02.12 22:20:51.280 (UTC+10) 3 (dns)   52.98.76.146
2020.02.12 22:20:51.280 (UTC+10) 3 (dns)   52.98.3.2
2020.02.12 22:20:51.280 (UTC+10) 3 (dns)   52.98.5.194
2020.02.12 22:20:51.280 (UTC+10) 3 Mail server address - 52.98.9.130, port 587
2020.02.12 22:20:51.280 (UTC+10) 3 State 5 -> 6
2020.02.12 22:20:51.280 (UTC+10) 3 Connecting ...
2020.02.12 22:20:51.287 (UTC+10) 3 Connected
2020.02.12 22:20:51.287 (UTC+10) 3 State 6 -> 9
2020.02.12 22:20:51.294 (UTC+10) 3 --[ raw ]-->

220 ME4P282CA0010.outlook.office365.com Microsoft ESMTP MAIL Service ready at Wed, 12 Feb 2020 11:20:49 +0000


2020.02.12 22:20:51.294 (UTC+10) 3 State 9 -> 10
2020.02.12 22:20:51.294 (UTC+10) 3 <--[ raw ]--

EHLO localhost


2020.02.12 22:20:51.294 (UTC+10) 3 sent
2020.02.12 22:20:51.300 (UTC+10) 3 --[ raw ]-->

250-ME4P282CA0010.outlook.office365.com Hello [124.178.35.191]

250-SIZE 157286400

250-PIPELINING

250-DSN

250-ENHANCEDSTATUSCODES

250-STARTTLS

250-8BITMIME

250-BINARYMIME

250-CHUNKING

250 SMTPUTF8


2020.02.12 22:20:51.300 (UTC+10) 3 Extensions :
2020.02.12 22:20:51.300 (UTC+10) 3   starttls - yes
2020.02.12 22:20:51.301 (UTC+10) 3   max_size - 157286400
2020.02.12 22:20:51.301 (UTC+10) 3   authent. - <none>
2020.02.12 22:20:51.301 (UTC+10) 3 State 10 -> 11
2020.02.12 22:20:51.301 (UTC+10) 3 <--[ raw ]--

STARTTLS


2020.02.12 22:20:51.301 (UTC+10) 3 sent
2020.02.12 22:20:51.306 (UTC+10) 3 --[ raw ]-->

220 2.0.0 SMTP server ready


2020.02.12 22:20:51.306 (UTC+10) 3 State 11 -> 12
2020.02.12 22:20:51.306 (UTC+10) 3 Securing ...
2020.02.12 22:20:51.306 (UTC+10) 3 (tls) init(), host = "smtp-mail.outlook.com", host_in_cert = ""
2020.02.12 22:20:51.307 (UTC+10) 3 (tls) <- 177
2020.02.12 22:20:51.307 (UTC+10) 3 (tls) handshake ...
2020.02.12 22:20:51.307 (UTC+10) 3 (tls) waiting for data ...
2020.02.12 22:20:51.314 (UTC+10) 3 (tls) -> 3935, total 3935
2020.02.12 22:20:51.316 (UTC+10) 3 (tls) InitializeSecurityContext() 00090312, 3935 bytes in, 133 bytes out
2020.02.12 22:20:51.316 (UTC+10) 3 (tls) <- 133
2020.02.12 22:20:51.316 (UTC+10) 3 (tls) waiting for data ...
2020.02.12 22:20:51.323 (UTC+10) 3 (tls) -> 51, total 51
2020.02.12 22:20:51.323 (UTC+10) 3 (tls) InitializeSecurityContext() 00000000, 51 bytes in, 0 bytes out
2020.02.12 22:20:51.323 (UTC+10) 3 (tls) handshake completed
2020.02.12 22:20:51.323 (UTC+10) 3 (tls) protocol - 00000800 - ?
2020.02.12 22:20:51.323 (UTC+10) 3       cipher   - 00006610 / 256 - AES
2020.02.12 22:20:51.323 (UTC+10) 3       digest   - 0000800d / 0 - SHA2
2020.02.12 22:20:51.323 (UTC+10) 3       exchange - 0000ae06 / 256 - ?
2020.02.12 22:20:51.323 (UTC+10) 3       cert :
2020.02.12 22:20:51.323 (UTC+10) 3        serial  - [07:21:61:dc:5b:e0:a4:81:e1:fb:38:37:3d:be:9b:ca]
2020.02.12 22:20:51.324 (UTC+10) 3        subject - [C=US, S=Washington, L=Redmond, O=Microsoft Corporation, CN=outlook.com]
2020.02.12 22:20:51.324 (UTC+10) 3        issuer  - [C=US, O=DigiCert Inc, CN=DigiCert Cloud Services CA-1]
2020.02.12 22:20:51.324 (UTC+10) 3 Secured
2020.02.12 22:20:51.324 (UTC+10) 3 State 12 -> 13
2020.02.12 22:20:51.324 (UTC+10) 3 <--[ tls ]--

bvck_it_up :

Feb 12, 2020

EHLO localhost


2020.02.12 22:20:51.324 (UTC+10) 3 (tls) <- 45
2020.02.12 22:20:51.324 (UTC+10) 3 sent
2020.02.12 22:20:51.330 (UTC+10) 3 (tls) -> 245, total 245
2020.02.12 22:20:51.330 (UTC+10) 3 (tls) decrypt() 245 bytes -> 00000000
2020.02.12 22:20:51.330 (UTC+10) 3 (tls) buf[0] = { type: 7, size: 13 bytes }
2020.02.12 22:20:51.331 (UTC+10) 3 (tls) buf[1] = { type: 1, size: 216 bytes }
2020.02.12 22:20:51.331 (UTC+10) 3 (tls) buf[2] = { type: 6, size: 16 bytes }
2020.02.12 22:20:51.331 (UTC+10) 3 (tls) buf[3] = { type: 0, size: 0 bytes }
2020.02.12 22:20:51.331 (UTC+10) 3 --[ tls ]-->

250-ME4P282CA0010.outlook.office365.com Hello [124.178.35.191]

250-SIZE 157286400

250-PIPELINING

250-DSN

250-ENHANCEDSTATUSCODES

250-AUTH LOGIN XOAUTH2

250-8BITMIME

250-BINARYMIME

250-CHUNKING

250 SMTPUTF8


2020.02.12 22:20:51.331 (UTC+10) 3 Extensions :
2020.02.12 22:20:51.331 (UTC+10) 3   starttls - NO
2020.02.12 22:20:51.331 (UTC+10) 3   max_size - 157286400
2020.02.12 22:20:51.331 (UTC+10) 3   authent. - xoauth2
2020.02.12 22:20:51.331 (UTC+10) 3 State 13 -> 14
2020.02.12 22:20:51.331 (UTC+10) 3 State 14 -> 15
2020.02.12 22:20:51.331 (UTC+10) 3 Logging in ...
2020.02.12 22:20:51.331 (UTC+10) 3 <--[ tls ]--

AUTH LOGIN


2020.02.12 22:20:51.331 (UTC+10) 3 (tls) <- 41
2020.02.12 22:20:51.331 (UTC+10) 3 sent
2020.02.12 22:20:51.337 (UTC+10) 3 (tls) -> 47, total 47
2020.02.12 22:20:51.337 (UTC+10) 3 (tls) decrypt() 47 bytes -> 00000000
2020.02.12 22:20:51.337 (UTC+10) 3 (tls) buf[0] = { type: 7, size: 13 bytes }
2020.02.12 22:20:51.337 (UTC+10) 3 (tls) buf[1] = { type: 1, size: 18 bytes }
2020.02.12 22:20:51.337 (UTC+10) 3 (tls) buf[2] = { type: 6, size: 16 bytes }
2020.02.12 22:20:51.337 (UTC+10) 3 (tls) buf[3] = { type: 0, size: 0 bytes }
2020.02.12 22:20:51.337 (UTC+10) 3 --[ tls ]-->

334 VXNlcm5hbWU6


2020.02.12 22:20:51.338 (UTC+10) 3 <--[ tls ]--

YnZja3VwX2FsZXJ0c0BvdXRsb29rLmNvbQ==


2020.02.12 22:20:51.338 (UTC+10) 3 (tls) <- 67
2020.02.12 22:20:51.338 (UTC+10) 3 sent
2020.02.12 22:20:51.344 (UTC+10) 3 (tls) -> 47, total 47
2020.02.12 22:20:51.344 (UTC+10) 3 (tls) decrypt() 47 bytes -> 00000000
2020.02.12 22:20:51.344 (UTC+10) 3 (tls) buf[0] = { type: 7, size: 13 bytes }
2020.02.12 22:20:51.344 (UTC+10) 3 (tls) buf[1] = { type: 1, size: 18 bytes }
2020.02.12 22:20:51.344 (UTC+10) 3 (tls) buf[2] = { type: 6, size: 16 bytes }
2020.02.12 22:20:51.344 (UTC+10) 3 (tls) buf[3] = { type: 0, size: 0 bytes }
2020.02.12 22:20:51.344 (UTC+10) 3 --[ tls ]-->

334 UGFzc3dvcmQ6


2020.02.12 22:20:51.344 (UTC+10) 3 <--[ tls ]--

  (22 bytes)

2020.02.12 22:20:51.345 (UTC+10) 3 (tls) <- 51
2020.02.12 22:20:51.345 (UTC+10) 3 sent
2020.02.12 22:20:56.749 (UTC+10) 3 (tls) -> 109, total 109
2020.02.12 22:20:56.749 (UTC+10) 3 (tls) decrypt() 109 bytes -> 00000000
2020.02.12 22:20:56.749 (UTC+10) 3 (tls) buf[0] = { type: 7, size: 13 bytes }
2020.02.12 22:20:56.749 (UTC+10) 3 (tls) buf[1] = { type: 1, size: 80 bytes }
2020.02.12 22:20:56.749 (UTC+10) 3 (tls) buf[2] = { type: 6, size: 16 bytes }
2020.02.12 22:20:56.749 (UTC+10) 3 (tls) buf[3] = { type: 0, size: 0 bytes }
2020.02.12 22:20:56.749 (UTC+10) 3 --[ tls ]-->

535 5.7.3 Authentication unsuccessful [ME4P282CA0010.AUSP282.PROD.OUTLOOK.COM]


2020.02.12 22:20:56.749 (UTC+10) 0 Non-2xx code: 535
2020.02.12 22:20:56.749 (UTC+10) 3 State 15 -> 20
2020.02.12 22:20:56.750 (UTC+10) 3 <--[ tls ]--

QUIT


2020.02.12 22:20:56.750 (UTC+10) 3 (tls) <- 35
2020.02.12 22:20:56.750 (UTC+10) 3 sent
2020.02.12 22:20:56.750 (UTC+10) 3 Shutting down TLS ...
2020.02.12 22:20:56.750 (UTC+10) 3 (tls) shutdown()
2020.02.12 22:20:56.750 (UTC+10) 3 (tls) handshake ...
2020.02.12 22:20:56.750 (UTC+10) 3 (tls) InitializeSecurityContext() 00000000, 0 bytes in, 31 bytes out
2020.02.12 22:20:56.750 (UTC+10) 3 (tls) <- 31
2020.02.12 22:20:56.750 (UTC+10) 3 (tls) handshake completed
2020.02.12 22:20:56.750 (UTC+10) 3 Shutting down TCP ...
2020.02.12 22:20:56.814 (UTC+10) 3 (tls) discard()

bvck_it_up :

Feb 12, 2020

Actually all good. Turns out I'm just a nong that didn't complete the rest of the initial mailbox creation before testing...

All working ok now!

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