Outlook / Hotmail Setup for Sending

[J-D-H]

I have several Hotmail accounts setup via the Outlook website. POPpeeper can receive Outlook / Hotmail email in two ways -- POP3 mode, or by using the POPpeeper webmail plugin. As far as I can tell, both of these work to receive email. However, although I used to be able to do this, I can no longer find a way which works to send email. When in SMTP mode, I have double checked the server address, port. etc., and these seem to be correct. Has anyone figured out how to get POPpeeper to work to both send and receive Outlook / Hotmail email?

[Jeff]

Whether you're using WebMail (for hotmail/outlook), POP3 or IMAP, SMTP is the only way to send email.

If you have POP Peeper v4.4, edit the account and for the "Server type" simply re-select what you already have selected -- this will force POP Peeper to reset the server settings to the "known good" values which should work.

If you still have a problem, let us know what the error is -- press the yellow '!' button on the bottom-right of the main window; then press the 'copy' button and use Paste in your reply.

[J-D-H]

I used to be able to receive and send emails using Hotmail -- why it no longer works escapes me. Here's the most recent error log entry:

--- Version ---
OS: Windows XP
POP Peeper: 4.4.0.0
Webmail: 4.4.2.0
SSL: 1.0.2.11
IMAP: 4.4.0.0
SendMail: 4.4.0.0

--- Error ---
Hotmail - J [0: POP3] ['pop-mail.outlook.com' (995) SSL: 1] [Smtp: 'smtp-mail.outlook.com' (587) SSL: 1] [Consec: 5]
- SSL connection failed (certificate failed: certificate has expired (10))
Send Mail: Could not connect to SMTP server

[mjs]

J-D-H, there is another POP Peeper update (v4.4.1.0) available that may resolve your problem, please click HERE for additional information on this at the bottom of this announcement topic.

[Jeff]

Actually, the latest install does not include the "full" list of certificates that you can download in the original message above the one that lakrsrool linked to (point #3).

However, I'm not sure if even the full list will work, because it's possible that the expired certificate that you have in the Windows certificate store will override it. I would actually be interested in knowing if this works for you or not, if you're willing to try it.

Possible Solution #2: Use IE8 (yes, IE8; not firefox, not IE6/7) and go to https://www.hotmail.com/
This *may* update your certificates; it may take a couple of minutes.
Again, I don't know if this will work for sure or not -- my test XP has already been updated with its certificates and pop-mail.hotmail.com works (without an updated cacerts.pem file) -- so I'd be interested in your results if you try this.

Guaranteed solution: Add pop-mail.outlook.com to the exceptions list (PP main menu: Tools / PPtweaker / Certificates); and you should add smtp-mail.outlook.com while you're at it. This solution bypasses the extra security that was added in v4.4.

[J-D-H]

I tried the 4.4.1 PP update, but still could not send email via Outlook/Hotmail. Then I saw that there was an update to the Webmail module (4.4.3), so I loaded that as well. I believe I am using the correct SMTP settings, but I still cannot send email via this account. Below is the log copy. If someone can interpret it, and if it implies anything interesting, please let me know.

--- Version ---
OS: Windows XP
POP Peeper: 4.4.1.0
Webmail: 4.4.3.0
SSL: 1.0.2.11
IMAP: 4.4.0.0
SendMail: 4.4.0.0

--- Error ---
Hotmail - J [1: Hotmail/Outlook] ['pop-mail.outlook.com' (993) SSL: 1] [Smtp: 'smtp-mail.outlook.com' (587) SSL: 1] [Consec: 5]
- No messages
Send Mail: Could not connect to SMTP server

[J-D-H]

I tried adding the certificate exception as suggested -- this did not help. Then I noticed that adding the the POP server line seemed wrong, so I went back and modified this to be a certificate exception for the SMTP server. I'm sorry to say that this did not work either. I am beginning to wonder if I have some simple setting wrongly set, but I have no clue what it might be. All I know is Hotmail/Outlook used to work in all respects. Here is the latest error log:

--- Version ---
OS: Windows XP
POP Peeper: 4.4.1.0
Webmail: 4.4.3.0
SSL: 1.0.2.11
IMAP: 4.4.0.0
SendMail: 4.4.0.0

--- Error ---
Hotmail - J [1: Hotmail/Outlook] ['pop-mail.outlook.com' (993) SSL: 1] [Smtp: 'smtp-mail.outlook.com' (587) SSL: 1] [Consec: 1]
- Send Mail: Could not connect to SMTP server
--------------------------------------------------------------
[MODERATOR NOTE - spc3rd]: I observe differences (shown in red font) in these last two error message posts, compared to the error message shown in red font in the 2nd post made near the top of this topic. Unsure of significance in this situation.

[mjs]

J-D-H - For some reason I am having problems with MSN accounts sending messages right now using "SSL/TLS" but I am able to send successfully using "STARTTLS".

So I would suggest that you change the "Send Mail" settings to use "STARTTLS" (doing this will automatically set the Port to "587", do not change the Port setting).

Example "Send Mail" settings that should work:

Try these "Send Mail" settings

Webmail automatic send settings.png (8.02 KiB) Viewed 4090 times

I'm assuming that you are able to receive incoming messages since you started using WebMail ("Hotmail/Outlook" Server setting) and that the only current problem is that you are unable to send messages, is this correct?

It appears to me that you should have been able to receive messages regarding your initial post with the settings you had using Port "995" with "SSL/TLS" using the "POP3" protocol but the error you were getting involved sending messages so I'm assuming the initial post involved this problem (which the above settings should address). Apparently at some point you later changed the Port to "993" which would be the incorrect port using "SSL/TLS" with "POP3" for receiving messages but regardless it appears you have since changed protocols once again regarding the last two posts and are now using the Webmail protocol (which I'm assuming now works for incoming messages).

As spc3rd pointed out, your Port setting changes would have impacted incoming messages during the time when you were using the POP3 protocol at some point before eventually switching to Webmail.

On that point J-D-H, when you change protocols ("Server type" to either "IMAP" or "POP3") are you changing other settings than just the "Server type"? I ask this because these other settings are automatically set so you should not have to change them (i.e. the Port settings) when you change protocols.

Please post back if you are still having problems receiving messages and more specifically sending messages using the above "Send Mail" settings.

[J-D-H]

Boy, you sure nailed it. I kept looking and looking at my settings, but for some reason I always "saw" SSL/TLS as STARTTLS. And I had already checked the Outlook/Hotmail website (several times, actually) and knew that STARTTLS was the correct setting! So now I feel like a real goof. Regardless, apologies to all here who tried to help. The problem was "selective symbol interpretation" all along!

John

J-D-H - For some reason I am having problems with MSN accounts sending messages right now using "SSL/TLS" but I am able to send successfully using "STARTTLS".

So I would suggest that you change the "Send Mail" settings to use "STARTTLS" (doing this will automatically set the Port to "587", do not change the Port setting).

Example "Send Mail" settings that should work:
Webmail automatic send settings.png I'm assuming that you are able to receive incoming messages since you started using WebMail ("Hotmail/Outlook" Server setting) and that the only current problem is that you are unable to send messages, is this correct?

It appears to me that you should have been able to receive messages regarding your initial post with the settings you had using Port "995" with "SSL/TLS" using the "POP3" protocol but the error you were getting involved sending messages so I'm assuming the initial post involved this problem (which the above settings should address). Apparently at some point you later changed the Port to "993" which would be the incorrect port using "SSL/TLS" with "POP3" for receiving messages but regardless it appears you have since changed protocols once again regarding the last two posts and are now using the Webmail protocol (which I'm assuming now works for incoming messages).

As spc3rd pointed out, your Port setting changes would have impacted incoming messages during the time when you were using the POP3 protocol at some point before eventually switching to Webmail.

On that point J-D-H, when you change protocols ("Server type" to either "IMAP" or "POP3") are you changing other settings than just the "Server type"? I ask this because these other settings are automatically set so you should not have to change them (i.e. the Port settings) when you change protocols.

Please post back if you are still having problems receiving messages and more specifically sending messages using the above "Send Mail" settings.