SMTP Outlook not working

Outlook 2010 client want to sent tru OS X Server.
Inkomming is working, outgoing is not working. Keeps error connection broken.
I have the following settings :
SMTP with SSL port 587
Trued numoruis combinations. I See in the server login conection refused wrong user name Digest-MD5 insteat of CRAM-MD5.
Accounts is working perfect on the Mac client. Same account.

Does the Apple Mac OS X Server: Microsoft Outlook clients may not be able to send mail (TS3023) tech note help?

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Primary - secondary smtp function not working

The text on my iPhone clearly states that should a primary smtp server not be working then the device will go on and try each of the secondary smtp servers in turn. However, long story short it sticks on the primary. I can see a number of posts on this issue here going back many months, but with no solution.
Does anyone yet know how to fix this? If not, aside from manually turning off the primary smtp server, what is the the best way to switch between outoing servers, e.g. from home wifi to town 'phone network, or vice versa?

Right i dont know if this helps or if this is what you are asking but?
But i dont send many emails when im out and about i always tend to send them when im in the house using my wi-fi, but one day i wanted to send an email whilst i was in work but it would'nt let me. Well to cut it short. My ISP wont let me use their server to send email once im out of the wi-fi range (so to speak) so someone from Macrumors told me to delete all my ISP details from the Outgoing server and then put in my Outgoing server, Primary Server, in the SMTP part.
Host name: smtp.o2.co.uk
Username: (this is your actual o2 website log-in name like) [email protected]
Password: (is you o2 log-in password)
try that, i hope this helps (or it is what you are talking about lol) mine works a treat now whilst im out of my wi-fi area.
Message was edited by: draperm25

Setting Out Of Office from Outlook not working with exchange 2010

Hi
We have an exchange 2010 server with 2 load balanced CAS server and Mailbox servers in a DAG. We have a few domain
names accepted (will call it firstdomain.com and seconddomain.com) but only one is in certificate (firstdomain.com).
The issue is - when user with default email @seconddomain.com try to set “Out Of Office” from outlook (2010 with all service
packs and updates) he is getting “ Your Out of Office settings cannot be displayed, because the server is currently unavailable. Try again later” where
setting it from webmail works fine and setting it from outlook for users with @firstdomain.com reply address works fine.
we have both internal and external urls for all virtual directories set to external
host address (https://mail.firstdomain.com
  etc). All the users are on intranet with local ip subnets (sites connected via vpns ), all the routing is in place and DNS points to correct ip addresses.
Autodiscover works fine (tested in outlook ) and giving correct address for OOF link
( https://mail.firstdomain.com/ews/exchange.asmx)
wich opens fine if entered into address bar in IE so its NOT AN AUTODISCOVER issue .
I enabled logging in outlook and thats what I am getting in there:
We have an exchange 2010 server with 2 load balanced CAS server and Mailbox servers in a DAG. We have a few domain
name accepted (will call it firstdomain.com and seconddomain.com) but only one is in certificate (firstdomain.com).
The issue is - when user with default email @seconddomain.com try to set “Out Of Office” from outlook (2010 with all service
packs and updates) he is getting “ Your Out of Office settings cannot be displayed, because the server is currently unavailable. Try again later” where
setting it from webmail works fine and setting it from outlook for users with @firstdomain.com reply address works fine.
we have both internal and external urls for all virtual directories set to external
host address (https://mail.firstdomain.com
  etc). All the users are on intranet with local ip subnets (sites connected via vpns ), all the routing is in place and DNS points to correct ip addresses.
Autodiscover works fine (tested in outlook ) and giving correct address for OOF link
( https://mail.firstdomain.com/ews/exchange.asmx)
wich opens fine if entered into address bar in IE so its NOT AN AUTODISCOVER issue .
I enabled logging in outlook and thats what I am getting in there:
1600       0x49763D20        02/02/15 16:50:44
+++++++++++++++++++++++++++++++
1600       0x49763D20        02/02/15 16:50:44
OWINHTTP SEND HTTP REQUEST BEGIN
1600       0x49763D20        02/02/15 16:50:44
Profile=Outlook
1600       0x49763D20        02/02/15 16:50:44
  [email protected]
1600       0x49763D20        02/02/15 16:50:44
URL=https://mail.firstdomain.com/ews/exchange.asmx
1600       0x49763D5F        02/02/15 16:50:45
GetLastError=0; httpStatus=401.
1600       0x49763D5F        02/02/15 16:50:45
OWinHtpp disabled auth schemes:
1600       0x49763D5F        02/02/15 16:50:45
<NONE>
1600       0x49763D5F        02/02/15 16:50:45
OWinHtpp supported auth schemes:
1600       0x49763D5F        02/02/15 16:50:45
Negotiate
1600       0x49763D5F        02/02/15 16:50:45
NTLM
1600       0x49763D5F        02/02/15 16:50:45
Basic
1600       0x49763D5F        02/02/15 16:50:45
OWinHttp attempting Auto-Negotiate with Desktop Credentials.
1600       0x49763D5F        02/02/15 16:50:45
OWinHttp USING pcreds->dwAuthScheme:
1600       0x49763D5F        02/02/15 16:50:45
Negotiate
1600       0x49763D9D       02/02/15 16:50:45
GetLastError=0; httpStatus=500.
1600       0x49763DAD       02/02/15 16:50:45
OWINHTTP SEND HTTP REQUEST END
1600       0x49763DAD       02/02/15 16:50:45
Last thing - we are using proxy server and with proxy off it works fine although all
possible exchange server hosts/domains/ip addresses excluded from proxy.
Aside from obvious question - what can be wrong and what to test next, another question
is - how can I check/monitor setting OOF on server side (log files etc)?
Last thing - we are using proxy server and with proxy off it works fine although all
possible exchange server hosts/domains/ip addresses excluded from proxy.
Aside from obvious question - what can be wrong and what to test next, another question
is - how can I check/monitor setting OOF on server side (log files etc)?
Thanks

Hi,
According to your description, I understand that Outlook client with second domain name cannot use OOF setting and get an error “Your Out of Office settings cannot be displayed, because the server is currently unavailable.” However OWA works fine.
If I misunderstand your concern, please do not hesitate to let me know.
I want to double confirm whether all account or some special user experience this question.
Would you please try to reconfigure Outlook profile in other Computer, Outlook version and return the results?
If this issue only appeared on Outlook 2010, please refer to below link to troubleshooting:
https://support.microsoft.com/kb/2596516?wa=wsignin1.0
Please try to run ExBPA to test OOF to get more details about this question. Additional, I find a similar thread about your question, for your reference:
https://social.technet.microsoft.com/Forums/exchange/en-US/81ebc1de-c899-4097-b224-a0e4b33e4162/users-cant-open-out-of-office-assistant
Best Regards,
Allen Wang

HT202304 SMTP Outgoing not working anymore?

Hello,
I was using the SMTP Outgoing settings for my NAS and Printer to send me notifications and this has stopped working recently. I've tried changing up the existing settings a bit but no luck. Tried SSL and TLS with no luck either. Using Port 587 and server smtp.mail.me.com. My NAS was using smtp.me.com in the past with success and was working fine. Any ideas?
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Does the Apple Mac OS X Server: Microsoft Outlook clients may not be able to send mail (TS3023) tech note help?

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First we have to know if you are using WiFi or Cellular network (3G or Edge).
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SMTP Outlook not working

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