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Outlook 2007 receiving but NOT sending email

Steve Mutchler
on
Outlook 2007...
Recieving but NOT sending emails...
Occasional Secuirty Certificate cannot be Verified...

My mother in law...age 95 is active on her PC...She uses Outlook and is fairly familiar with it...We POP Gmail...

She has been using this PC with W7 and Outlook 2007 for about 8 years...
She lives in an assisted care facility...

About 2 weeks ago she started getting Security Certificate cannot be Verified...
Relates to Sophos...says a mismatch in the SSL port...and Outlook will NOT send email...but she recieves email ok...

I cleaned it up...reinstalled Office 2007...and got the same problem...no joy...

So...I took it to my shop...and discovered that Outlook worked just fine on MY internet connection...

BUT....I rebuild the PC anyway and installed W10...re-installed Outlook 2007...connected her PST file and everything is working perfectly on MY internet...

I set it up again in her apartment at the assisted care facility and Outlook will NOT send email...I had the facilities maintenance guy try...and we cannot get it working...
Internet is fine...if I go to Gmai webmail her email works just fine...

So...It seems to be an Outlook issue on the facilities network...

So...on Gmail the SMTP port is 587....what do you think the chances are that the IT company that handles the assisted care facility closed port 587 on the router...???

Or...is there some possible other reason for the issue...

Many thanks in advance...
Amber-gmail-settings.docx
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JohnBusiness Consultant (Owner)
Most Valuable Expert 2012
Expert of the Year 2018

Commented:
Outlook sends on your connection, not on her connection.

You have set SMTP on port 587 and then Auto, STARTTLS or, … ?

what do you think the chances are that the IT company that handles the assisted care facility closed port 587 on the router

You would have to ask them, and also check what security is being used on port 587. Maybe it needs to be changed. Can you use port 465 / TLS?

Author

Commented:
SMTP is 587 TLS...
495 on SSL works on my inet but NOT on hers...
Here is the link to the Gmail settings...
https://support.google.com/mail/answer/7104828?hl=en
I have everything correct...
And I have probably 50 clients that run Outlook from 2003 thru 2016...most of them POP from Gmail but some from
other sources...never has an issue like this....
JohnBusiness Consultant (Owner)
Most Valuable Expert 2012
Expert of the Year 2018

Commented:
I read the Gmail settings (and understand).

Try 465 / TLS to see - I used that once myself. Probably not but try.

Then contact the Home's ISP because it does look like they may have blocked it.
CERTIFIED EXPERT
Top Expert 2015

Commented:
It does sounds like the router is blocking those ports but you can test this.  Download openssl and test to see if you can send email out.  If they block the port you won't even get the EHLO response.

https://stackoverflow.com/questions/11046135/how-to-send-email-using-simple-smtp-commands-via-gmail

Author

Commented:
Set up telnet on my pc...w10...
ran     telnet google.com 25...........could not open connection to host
ran     telnet google.com 587.........could not open connection to host

So...google should block port 25 and it seems like it did...
But 587 is googles ssl connection and that should show some indication that it's working....

Wayne88...I don;t want to send mail using smtp commands...I only want to find out if the assisted care facility is blocking port 587
on their router....whatever commands I run will have to be at the facility...probably won't be able to get there until this weekend to test...
But I'm testing on MY computer so I know what to expect when I get to Grandma's place...

Author

Commented:
I also ran Shields Up...but that is not giving me any useful information...

There should be a simple command that I can run from Grandma's comptuer at her apartment at the assisted care facility that
can check if their router is blocking 587....If I can determine that 587 IS blocked...I can take that info to management and have them
ask their IT guys to unblock that port...
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Top Expert 2015

Commented:
"Wayne88...I don;t want to send mail using smtp commands"

This is for testing to see if the TLS port is open and if it is then you will get a response from the gmail server.  In the link I provided it showed you the steps to accomplish this.

Please read the link.  Your telnet test won't work.

"to send over gmail, you need to use an encrypted connection. this is not possible with telnet alone, but you can use tools like openssl"

If you can't get a response from the gmail server using the steps provided then something is blocked somewhere and chances are it's the router at the location.

Author

Commented:
Wayne88....I must confess my skill level for this stuff is very weak...I looked thru your link...This is more than I can handle...

I tried Shields Up on MY computer with MY router and from those results I don;'t think 587 is open on my router and i use Gmail...

so.........I don;t know what to do from here...
Sorry...

Author

Commented:
Ok...still banging away on this...
I tried....telnet smtp.gmail.com 587 and got a 220  smtp.com ESMTP 189-v6sm879606itl.10 - gsmtp....so it looks like that works...
JohnBusiness Consultant (Owner)
Most Valuable Expert 2012
Expert of the Year 2018

Commented:
Can you set Outlook to mimic this in terms of Ports / Security?

You still need to talk to the Home ISP to see what they are doing.

Author

Commented:
It will be Saturday before I can get to grandma and test my telnet connection...
If I don;t get a connection then I'll have to take it up with the manager of the facility...

Thanks everyone for your help and suggestions...
I'll post back on Sat sometime and let you know what happened...
CERTIFIED EXPERT
Commented:
Ask IT guys for SMTP interception.
Possible they install a "sophos UTM" and you have to deal with their certificates to build the trust relationship with gmail.
Would you post the SSL-error message?

Author

Commented:
I don't have a copy of the SSL error...but Sophos is mentioned...
The verbage is something like this...

"the server you are connected to is using a security certificate that cannot  be verified"
There is a button to View Certificate...
And under details Sophos is listed...but I don't remember any other verbage with the sophos...

It might have said SophosUTM...not sure...

The facility is rather small...about 80 residents...I don;t know yet who the contract their IT out to...
But I'm thinking it's probably not a large firm...trying to keep IT costs down...so I'm think they
prolly would not install the SophosUTM system...

I'll know more Saturday...

Thanks for the help...

Author

Commented:
Ok...this seems to be the deal...
Grandma's pc Outlook 2007 is working PERFECTLY on my inet connection...
I set it back up in her apartment today and Outlook 2007 will NOT send email...receives email ok...on inet ok...

So I ran this test.....telnet smtp.gmail.com 587 and got a reply  220 sophosESMTP....cursor waits for input...I had nothing to input... so I quit...
CMD prompt returns...so from this test...her pc connects to Sophos something or other and waits for another command...

So...I think the IT service company that handles the retirement complex's network installed SophosUTM about 6 weeks ago which is about when the issue of SMTP not working on port 587 for Outlook to send email...

I talked to front office...gave them my card...explained the issue...and told them that they can have their IT folks call me if they want...

Hopefully this will be worked out within a week or so...

Many thanks for all the help...
JohnBusiness Consultant (Owner)
Most Valuable Expert 2012
Expert of the Year 2018

Commented:
Please keep us advised and if it is all working now please let us know

Author

Commented:
I will...I'm guessing this is a problem that nobody has run into before....
Hopefully we will learn something to be applied to similar issues...
JohnBusiness Consultant (Owner)
Most Valuable Expert 2012
Expert of the Year 2018

Commented:
So long as I use the ISP mail settings it all works, and since it works on your internet, then it appears to be your grandmother's Home ISP issues.

Author

Commented:
John...I agree...Hopefully whomever handles the IT for the facility will call me Monday and we can talk about the issue...
CERTIFIED EXPERT
Top Expert 2015

Commented:
It's most likely the Sophos UTM and they probably didn't expect anyone to use Outlook with email or require port 587.  They probably thought most people there will just use webmail.

Author

Commented:
Wayne88....I expect  you are correct...
I really am not familiar with SohosUTM...did a little reading on it...and it seems like a good security product...but I really don;t know...

There are about 70 people in the facility...and from what I can determine...most on webmail...and a few on Outlook but not popping
gmail...Yahoo...and a couple of others that don't need 587...

Should know more next week...
CERTIFIED EXPERT
Top Expert 2015

Commented:
Thanks for getting back and please let us know how it goes.

Author

Commented:
Quick update...
Still waiting on info from the assisted care facility...
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Top Expert 2015

Commented:
No worries.  We're here if you have any questions.

Author

Commented:
Nobody has contacted me yet and when I talked with my mother in law yesterday...nobody had talked to her...
So...another trip out there and secure a meeting with the administrator of the facility and see what I can do...
CERTIFIED EXPERT

Commented:
The point where you See the ssl-error and zertificate details, you are able to install the certificate as "trusted" from here?

Author

Commented:
Dirk...Doesn;t work...

Author

Commented:
Ok...we are fixed....Turns out that they had a proxy server running Sophos UTM for some time....somebody made some adjustments of some kind and "accidently" closed 587....I did not have a chance to talk with the supporting techs....but the info I got back essentially confirms what we had pretty much decided was the answer....

Grandma is sending out emails at a record clip since she has been blocked for about 7 weeks...

Thanks for all you help and suggestions...
CERTIFIED EXPERT
Top Expert 2015

Commented:
Glad you got to the bottom of it.  Cheers!