Outlook prompting for password with new Exchange 2013

I have Exchange 2007 and 2013. I want to migrate to 2013 but I'm having issues in the testing phase. I have a test account that I moved the mailbox to the new server. I have a test PC with a modified hosts file that points to the new Exch
2013 server IP address.
When I log in with this test user, Outlook appears to connect and download the mailbox. However a Windows Security dialog box pops up saying Microsoft Outlook Connecting to [email protected] and it has a username and password field. No matter what
is entered here, it is NOT accepted, nor if forcefully entering the wrong information is the account locked out.
I can click cancel here and it proceeds to update the inbox and then says All folders are up to date. But at the bottom in Outlook 2013 it says Need password and Outlook's icon in the taskbar has a yellow triangle on it. I can send myself a test
email and I get it (I personally am on the 2007 server), but after it sends Outlook 2013 prompts again for the password, and since it does not accept anything, I have to click cancel.
I have done ALL the windows updates available on this test PC. Exchange 2013 is on CU6 which is the latest at the time of this writing.
Another thing is in the Lync 2013 client it says "Exchange needs your credentials". No matter what is entered here, it will not make this message go away unless you click the X on this warning bar. Lync itself appears to work regardless.
Any ideas?
I just changed the ExternalClientAuthenticationMethod from Ntlm to Negotiage. Now the Outlook prompt does accept the domain password, but I don't want anyone to have to enter any type of credentials just to get on. Note, this test is on the same
LAN as the servers, so I haven't even tackled an external test yet, though last time I tried it was the same results.

Ok besides LYNC 2013 asking for exchange credentials, I cannot get Outlook to work externally.
Externally to the NEW Exch2013 server, we are trying something different this time around. Instead of poking port 443 straight to the Exchange server from the outside world, we are trying what we did with LYNC. We are poking port 443 to an IIS
AAR reverse proxy to it's DMZ interface. It has another nic on DMZ 2 which allows port 443 to the Exchange 2013 server.
So I can use this with no problem for OWA if using an account on the new 2013 Exchange server. But if using an account on the old Exchange server, after I click sign in I get "The webpage at https://legacy.domain.com/owa/auth/owaauth.dll might
be temporarily down or it may have moved permanently to a new web address. ERR_RESPONSE_HEADERS_TRUNCATED.
Then of course Outlook Anywhere does not work. After I put in my password it sits there trying to connect with nothing.
Here is part of the IIS log on the AAR server.
#Software: Microsoft Internet Information Services 7.5
#Version: 1.0
#Date: 2014-10-24 20:00:02
#Fields: date time s-ip cs-method cs-uri-stem cs-uri-query s-port cs-username c-ip cs(User-Agent) sc-status sc-substatus sc-win32-status time-taken
2014-10-24 20:00:02 192.168.1.13 OPTIONS /Microsoft-Server-ActiveSync User=exchange2007user&DeviceId=BAEEF5AE6A1CE1C61A2E62E992691FE2&DeviceType=WindowsMail&X-ARR-CACHE-HIT=0&X-ARR-LOG-ID=6301e6ce-7827-42cd-91a4-7eaa47ac659c 443 - 192.168.50.240 WindowsMail/17.5.9600.20605 500 0 0 19390
2014-10-24 20:00:02 192.168.1.13 POST /autodiscover/autodiscover.xml X-ARR-CACHE-HIT=0&X-ARR-LOG-ID=36d2360b-79c5-4ca0-a250-08b892cd5b70 443 - 192.168.50.240 WindowsMail/17.5.9600.20605 401 0 0 0
2014-10-24 20:00:08 192.168.1.13 RPC_IN_DATA /rpc/rpcproxy.dll mail.domain.com:6002&X-ARR-CACHE-HIT=0&X-ARR-LOG-ID=7615e512-4e58-424b-8ce1-654ba86bfe2e 443 - 192.168.50.240 MSRPC 401 0 0 31
2014-10-24 20:00:08 192.168.1.13 RPC_IN_DATA /rpc/rpcproxy.dll mail.domain.com:6002 443 - 192.168.50.240 MSRPC 404 13 0 0
2014-10-24 20:00:08 192.168.1.13 RPC_OUT_DATA /rpc/rpcproxy.dll mail.domain.com:6002&X-ARR-CACHE-HIT=0&X-ARR-LOG-ID=c3f94f7d-b408-4ff9-9de0-3e4577829b97 443 - 192.168.50.240 MSRPC 401 0 0 46
2014-10-24 20:00:22 192.168.1.13 POST /Microsoft-Server-ActiveSync eQAJBBC67vWuahzhxhouYumSaR/iBK6gyiwLV2luZG93c01haWw=&X-ARR-CACHE-HIT=0&X-ARR-LOG-ID=0b1ef554-5b08-4e0a-a9bd-294601364f4a 443 - 192.168.50.240 WindowsMail/17.5.9600.20605 500 0 0 19047
2014-10-24 20:00:22 192.168.1.13 POST /autodiscover/autodiscover.xml X-ARR-CACHE-HIT=0&X-ARR-LOG-ID=b1fa8dde-9c16-40b9-9932-f49e7dc971c4 443 - 192.168.50.240 WindowsMail/17.5.9600.20605 401 0 0 0
2014-10-24 20:00:41 192.168.1.13 OPTIONS /Microsoft-Server-ActiveSync User=exchange2007user&DeviceId=BAEEF5AE6A1CE1C61A2E62E992691FE2&DeviceType=WindowsMail&X-ARR-CACHE-HIT=0&X-ARR-LOG-ID=8b94ec84-08dc-43e3-aeae-d00b1e4c9837 443 - 192.168.50.240 WindowsMail/17.5.9600.20605 500 0 0 19047
2014-10-24 20:00:41 192.168.1.13 POST /autodiscover/autodiscover.xml X-ARR-CACHE-HIT=0&X-ARR-LOG-ID=1412decf-d570-440a-9ac4-8a6347b18bbd 443 - 192.168.50.240 WindowsMail/17.5.9600.20605 401 0 0 0
2014-10-24 20:01:00 192.168.1.13 POST /Microsoft-Server-ActiveSync eQAJBBC67vWuahzhxhouYumSaR/iBK6gyiwLV2luZG93c01haWw=&X-ARR-CACHE-HIT=0&X-ARR-LOG-ID=5d1754fc-cc71-43fe-876d-2eff7ba1efbf 443 - 192.168.50.240 WindowsMail/17.5.9600.20605 500 0 0 19032
2014-10-24 20:01:00 192.168.1.13 POST /autodiscover/autodiscover.xml X-ARR-CACHE-HIT=0&X-ARR-LOG-ID=a8609c9a-6fc3-43d1-b961-74e95dc53bf1 443 - 192.168.50.240 WindowsMail/17.5.9600.20605 401 0 0 0
2014-10-24 20:01:09 192.168.1.13 RPC_OUT_DATA /rpc/rpcproxy.dll mail.domain.com:6002&X-ARR-LOG-ID=cdcb7486-bdad-4f66-a300-3d1262be606a 443 - 192.168.50.240 MSRPC 200 0 0 60138
2014-10-24 20:01:11 192.168.1.13 RPC_IN_DATA /rpc/rpcproxy.dll mail.domain.com:6001&X-ARR-CACHE-HIT=0&X-ARR-LOG-ID=3ac5ff66-5ad1-495d-9293-5bc3540b481c 443 - 192.168.50.240 MSRPC 401 0 0 46
2014-10-24 20:01:11 192.168.1.13 RPC_IN_DATA /rpc/rpcproxy.dll mail.domain.com:6001 443 - 192.168.50.240 MSRPC 404 13 0 0
2014-10-24 20:01:11 192.168.1.13 RPC_OUT_DATA /rpc/rpcproxy.dll mail.domain.com:6001&X-ARR-CACHE-HIT=0&X-ARR-LOG-ID=b8b39056-6c89-48ec-98d9-0456aad716f1 443 - 192.168.50.240 MSRPC 401 0 0 78
2014-10-24 20:02:11 192.168.1.13 RPC_OUT_DATA /rpc/rpcproxy.dll mail.domain.com:6001&X-ARR-LOG-ID=44351254-c944-45ab-9b6f-e020358b993b 443 - 192.168.50.240 MSRPC 200 0 0 60184
2014-10-24 20:02:11 192.168.1.13 RPC_IN_DATA /rpc/rpcproxy.dll MAIL:6002&X-ARR-CACHE-HIT=0&X-ARR-LOG-ID=20e05c35-5b55-461f-9b9e-7e85b2266269 443 - 192.168.50.240 MSRPC 401 0 0 31
2014-10-24 20:02:11 192.168.1.13 RPC_IN_DATA /rpc/rpcproxy.dll MAIL:6002 443 - 192.168.50.240 MSRPC 404 13 0 15
2014-10-24 20:02:11 192.168.1.13 RPC_OUT_DATA /rpc/rpcproxy.dll MAIL:6002&X-ARR-CACHE-HIT=0&X-ARR-LOG-ID=079dc1e7-6edf-43d9-8d92-67229c259c93 443 - 192.168.50.240 MSRPC 401 0 0 31
2014-10-24 20:03:11 192.168.1.13 RPC_OUT_DATA /rpc/rpcproxy.dll MAIL:6002&X-ARR-LOG-ID=9cef3d08-4052-45f5-8806-3a6729818138 443 - 192.168.50.240 MSRPC 200 0 0 60169
2014-10-24 20:03:13 192.168.1.13 RPC_IN_DATA /rpc/rpcproxy.dll mail.domain.com:6002&X-ARR-CACHE-HIT=0&X-ARR-LOG-ID=4bdb9a31-c8bc-4174-9958-4daaea796edb 443 - 192.168.50.240 MSRPC 401 0 0 46
2014-10-24 20:03:13 192.168.1.13 RPC_IN_DATA /rpc/rpcproxy.dll mail.domain.com:6002 443 - 192.168.50.240 MSRPC 404 13 0 0
2014-10-24 20:03:13 192.168.1.13 RPC_OUT_DATA /rpc/rpcproxy.dll mail.domain.com:6002&X-ARR-CACHE-HIT=0&X-ARR-LOG-ID=d1489811-2925-458f-910d-702746329d0c 443 - 192.168.50.240 MSRPC 401 0 0 31
2014-10-24 20:04:13 192.168.1.13 RPC_OUT_DATA /rpc/rpcproxy.dll mail.domain.com:6002&X-ARR-LOG-ID=545f6dff-9eff-4353-939d-20b3caf50d3f 443 - 192.168.50.240 MSRPC 200 0 0 60169
2014-10-24 20:04:13 192.168.1.13 RPC_IN_DATA /rpc/rpcproxy.dll DC1.domain.com:6004&X-ARR-CACHE-HIT=0&X-ARR-LOG-ID=86b53049-82f2-44b8-9135-bb54d02fbaae 443 - 192.168.50.240 MSRPC 401 0 0 31
2014-10-24 20:04:13 192.168.1.13 RPC_IN_DATA /rpc/rpcproxy.dll DC1.domain.com:6004 443 - 192.168.50.240 MSRPC 404 13 0 15
2014-10-24 20:04:13 192.168.1.13 RPC_OUT_DATA /rpc/rpcproxy.dll DC1.domain.com:6004&X-ARR-CACHE-HIT=0&X-ARR-LOG-ID=1a4eefbd-de59-4fac-b7de-8df5fb2e323b 443 - 192.168.50.240 MSRPC 401 0 0 31
2014-10-24 20:04:13 192.168.1.13 RPC_OUT_DATA /rpc/rpcproxy.dll DC1.domain.com:6004&X-ARR-LOG-ID=83dac450-4479-40d4-8cb9-e82e36085dbe 443 - 192.168.50.240 MSRPC 404 0 0 31
2014-10-24 20:04:15 192.168.1.13 RPC_IN_DATA /rpc/rpcproxy.dll MAIL:6001&X-ARR-CACHE-HIT=0&X-ARR-LOG-ID=b3fd8e85-122e-47b8-85e8-cfbc1281aa1d 443 - 192.168.50.240 MSRPC 401 0 0 62
2014-10-24 20:04:15 192.168.1.13 RPC_IN_DATA /rpc/rpcproxy.dll MAIL:6001 443 - 192.168.50.240 MSRPC 404 13 0 0
2014-10-24 20:04:15 192.168.1.13 RPC_OUT_DATA /rpc/rpcproxy.dll MAIL:6001&X-ARR-CACHE-HIT=0&X-ARR-LOG-ID=eaee2bf9-cc0e-4805-b715-befb335ed25c 443 - 192.168.50.240 MSRPC 401 0 0 46
2014-10-24 20:05:15 192.168.1.13 RPC_OUT_DATA /rpc/rpcproxy.dll MAIL:6001&X-ARR-LOG-ID=535cdb59-c23f-44ae-ada8-9f07bca29f92 443 - 192.168.50.240 MSRPC 200 0 0 60169
2014-10-24 20:05:15 192.168.1.13 RPC_IN_DATA /rpc/rpcproxy.dll mail.domain.com:6004&X-ARR-CACHE-HIT=0&X-ARR-LOG-ID=f2d73aad-ba0e-413d-bff0-713bc830f028 443 - 192.168.50.240 MSRPC 401 0 0 46
2014-10-24 20:05:15 192.168.1.13 RPC_IN_DATA /rpc/rpcproxy.dll mail.domain.com:6004 443 - 192.168.50.240 MSRPC 404 13 0 15
2014-10-24 20:05:15 192.168.1.13 RPC_OUT_DATA /rpc/rpcproxy.dll mail.domain.com:6004&X-ARR-CACHE-HIT=0&X-ARR-LOG-ID=93219c6c-bbab-49ae-b12a-4c8f7939368c 443 - 192.168.50.240 MSRPC 401 0 0 31
2014-10-24 20:05:46 192.168.1.13 POST /autodiscover/autodiscover.xml X-ARR-CACHE-HIT=0&X-ARR-LOG-ID=a9d7e8b9-6f0e-4036-b6ff-298fb483dffc 443 - 192.168.50.240 Microsoft+Office/15.0+(Windows+NT+6.2;+Microsoft+Outlook+15.0.4659;+Pro) 401 0 0 62
2014-10-24 20:06:07 192.168.1.13 POST /autodiscover/autodiscover.xml X-ARR-CACHE-HIT=0&X-ARR-LOG-ID=a79a1894-554c-496f-98b5-8935644f286b 443 - 192.168.50.240 Microsoft+Office/15.0+(Windows+NT+6.2;+Microsoft+Outlook+15.0.4659;+Pro) 401 0 0 46
2014-10-24 20:06:07 192.168.1.13 POST /autodiscover/autodiscover.xml X-ARR-CACHE-HIT=0&X-ARR-LOG-ID=6dab43de-a34f-426f-ba56-a7b589c8a5c9 443 - 192.168.50.240 Microsoft+Office/15.0+(Windows+NT+6.2;+Microsoft+Outlook+15.0.4659;+Pro) 401 0 0 15
2014-10-24 20:06:07 192.168.1.13 POST /autodiscover/autodiscover.xml X-ARR-CACHE-HIT=0&X-ARR-LOG-ID=d7323b0f-5af4-4741-88ac-07e51675feaf 443 - 192.168.50.240 Microsoft+Office/15.0+(Windows+NT+6.2;+Microsoft+Outlook+15.0.4659;+Pro) 401 0 0 15
2014-10-24 20:06:07 192.168.1.13 POST /autodiscover/autodiscover.xml X-ARR-CACHE-HIT=0&X-ARR-LOG-ID=d27bd9f8-2292-4710-b1ce-1f613733af8b 443 - 192.168.50.240 Microsoft+Office/15.0+(Windows+NT+6.2;+Microsoft+Outlook+15.0.4659;+Pro) 401 0 0 0
2014-10-24 20:06:07 192.168.1.13 POST /autodiscover/autodiscover.xml X-ARR-CACHE-HIT=0&X-ARR-LOG-ID=c9a1d015-6ec5-469b-b6f0-1e2532b36b54 443 - 192.168.50.240 Microsoft+Office/15.0+(Windows+NT+6.2;+Microsoft+Outlook+15.0.4659;+Pro) 401 0 0 62
2014-10-24 20:06:16 192.168.1.13 RPC_OUT_DATA /rpc/rpcproxy.dll mail.domain.com:6004&X-ARR-LOG-ID=29d563b7-b6b9-4600-8344-5afd6af2e1d7 443 - 192.168.50.240 MSRPC 200 0 0 60184
2014-10-24 20:07:36 192.168.1.13 POST /autodiscover/autodiscover.xml X-ARR-CACHE-HIT=0&X-ARR-LOG-ID=2af97edd-0e95-41d9-b55f-84f0b98d9a8d 443 - 192.168.50.240 Microsoft+Office/15.0+(Windows+NT+6.2;+Microsoft+Outlook+15.0.4659;+Pro) 401 0 0 46
2014-10-24 20:07:36 192.168.1.13 POST /autodiscover/autodiscover.xml X-ARR-LOG-ID=4524480e-1bca-4e48-b807-ba39a1c5c934 443 - 192.168.50.240 Microsoft+Office/15.0+(Windows+NT+6.2;+Microsoft+Outlook+15.0.4659;+Pro) 200 0 0 468
2014-10-24 20:07:37 192.168.1.13 RPC_IN_DATA /rpc/rpcproxy.dll MAIL:6004&X-ARR-CACHE-HIT=0&X-ARR-LOG-ID=7d07ec9d-7d0b-4d2a-a742-7c3552b267f9 443 - 192.168.50.240 MSRPC 401 0 0 78
2014-10-24 20:07:37 192.168.1.13 RPC_IN_DATA /rpc/rpcproxy.dll MAIL:6004 443 - 192.168.50.240 MSRPC 404 13 0 0
2014-10-24 20:07:37 192.168.1.13 RPC_OUT_DATA /rpc/rpcproxy.dll MAIL:6004&X-ARR-CACHE-HIT=0&X-ARR-LOG-ID=804dc16d-37a9-44a1-91fc-462336f7ff69 443 - 192.168.50.240 MSRPC 401 0 0 46
2014-10-24 20:08:38 192.168.1.13 RPC_OUT_DATA /rpc/rpcproxy.dll MAIL:6004&X-ARR-LOG-ID=95a61f86-fdc2-4868-ae7a-25505f4c131c 443 - 192.168.50.240 MSRPC 200 0 0 60138
2014-10-24 20:08:40 192.168.1.13 RPC_IN_DATA /rpc/rpcproxy.dll mail.domain.com:6001&X-ARR-CACHE-HIT=0&X-ARR-LOG-ID=e7007c02-bc0a-4b04-906e-29c653796099 443 - 192.168.50.240 MSRPC 401 0 0 46
2014-10-24 20:08:40 192.168.1.13 RPC_IN_DATA /rpc/rpcproxy.dll mail.domain.com:6001 443 - 192.168.50.240 MSRPC 404 13 0 0
2014-10-24 20:08:40 192.168.1.13 RPC_OUT_DATA /rpc/rpcproxy.dll mail.domain.com:6001&X-ARR-CACHE-HIT=0&X-ARR-LOG-ID=2495013e-d003-4dcd-8dc4-b5756acf0618 443 - 192.168.50.240 MSRPC 401 0 0 31
2014-10-24 20:08:46 192.168.1.13 POST /autodiscover/autodiscover.xml X-ARR-CACHE-HIT=0&X-ARR-LOG-ID=fc7f2ec4-3af1-4059-997e-fd18680c6f94 443 - 192.168.50.240 Microsoft+Office/15.0+(Windows+NT+6.2;+Microsoft+Outlook+15.0.4659;+Pro) 401 0 0 46
2014-10-24 20:08:46 192.168.1.13 POST /autodiscover/autodiscover.xml X-ARR-LOG-ID=4f75729e-bf92-499c-8dc2-832fddc27582 443 - 192.168.50.240 Microsoft+Office/15.0+(Windows+NT+6.2;+Microsoft+Outlook+15.0.4659;+Pro) 200 0 0 46
2014-10-24 20:08:46 192.168.1.13 RPC_IN_DATA /rpc/rpcproxy.dll mail.domain.com:6002&X-ARR-CACHE-HIT=0&X-ARR-LOG-ID=327a2992-2b43-41ff-9ac4-a9960daba60d 443 - 192.168.50.240 MSRPC 401 0 0 31
2014-10-24 20:08:46 192.168.1.13 RPC_IN_DATA /rpc/rpcproxy.dll mail.domain.com:6002 443 - 192.168.50.240 MSRPC 404 13 0 0
2014-10-24 20:08:46 192.168.1.13 RPC_OUT_DATA /rpc/rpcproxy.dll mail.domain.com:6002&X-ARR-CACHE-HIT=0&X-ARR-LOG-ID=784171c0-def0-4369-a9ad-374a25a21801 443 - 192.168.50.240 MSRPC 401 0 0 46
2014-10-24 20:09:10 192.168.1.13 POST /autodiscover/autodiscover.xml X-ARR-CACHE-HIT=0&X-ARR-LOG-ID=2399c7d5-50e2-4c0f-85ed-ffeb92f411a8 443 - 192.168.50.240 Microsoft+Office/15.0+(Windows+NT+6.2;+Microsoft+Outlook+15.0.4659;+Pro) 401 0 0 31
2014-10-24 20:09:10 192.168.1.13 POST /autodiscover/autodiscover.xml X-ARR-CACHE-HIT=0&X-ARR-LOG-ID=0156ccf0-043c-4c45-83db-f62cde770079 443 - 192.168.50.240 Microsoft+Office/15.0+(Windows+NT+6.2;+Microsoft+Outlook+15.0.4659;+Pro) 401 0 0 0
2014-10-24 20:09:10 192.168.1.13 POST /autodiscover/autodiscover.xml X-ARR-CACHE-HIT=0&X-ARR-LOG-ID=40934ba2-41f8-435f-b62e-ababb51e00e2 443 - 192.168.50.240 Microsoft+Office/15.0+(Windows+NT+6.2;+Microsoft+Outlook+15.0.4659;+Pro) 401 0 0 31
2014-10-24 20:09:10 192.168.1.13 POST /autodiscover/autodiscover.xml X-ARR-CACHE-HIT=0&X-ARR-LOG-ID=049938a4-cc8a-4476-b123-2d2a2dbcbcf7 443 - 192.168.50.240 Microsoft+Office/15.0+(Windows+NT+6.2;+Microsoft+Outlook+15.0.4659;+Pro) 401 0 0 0
2014-10-24 20:09:10 192.168.1.13 POST /autodiscover/autodiscover.xml X-ARR-CACHE-HIT=0&X-ARR-LOG-ID=232d57a3-e1e3-43eb-8f04-ffc8f57c9359 443 - 192.168.50.240 Microsoft+Office/15.0+(Windows+NT+6.2;+Microsoft+Outlook+15.0.4659;+Pro) 401 0 0 0
2014-10-24 20:09:10 192.168.1.13 POST /autodiscover/autodiscover.xml X-ARR-CACHE-HIT=0&X-ARR-LOG-ID=186a6668-8ce2-415b-8b1c-a2a2cb246617 443 - 192.168.50.240 Microsoft+Office/15.0+(Windows+NT+6.2;+Microsoft+Outlook+15.0.4659;+Pro) 401 0 0 46
2014-10-24 20:09:10 192.168.1.13 POST /autodiscover/autodiscover.xml X-ARR-LOG-ID=a5697f0e-972e-4e2f-8149-667cc7c4cee5 443 - 192.168.50.240 Microsoft+Office/15.0+(Windows+NT+6.2;+Microsoft+Outlook+15.0.4659;+Pro) 200 0 0 31

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Open Control Panel, then choose Mail.
Click Email Account and then choose the account.
Click Change and then Click More Settings.
Choose Security tap and change the Logon network security to
Negotiate Authentication.
Unchecked the box that states Always prompt for login credentials.
Here is a thread for reference:
http://social.technet.microsoft.com/Forums/en-US/8137153c-abe1-4c33-aa44-e90cdd761e01/outlook-keeps-prompting-for-password?forum=exchange2010
If this issue persists, please let me know.

Outlook prompts for password

Hi
We are in a migration of Exchange 2007 to Exchange 2013, so for the moment it is a coexistence.
I migrated 2 mailboxes to Exchange 2013. After the migration, outlook started prompting for a password by starting outlook. Once the password has been entered, outlook works fine. But that happens only if outlook cache mode is active. If I disable cached
mode, outlook starts without prompting for a password.
So I deactivated cached mode, deleted the ost file and again activated cached mode. Now Outlook starts without prompting for a password, even if cached mode is active.
Deleting the ost file for 1 or 2 users is fine, but not if there are 200 more mailboxes to migrate.
I cannot reproduce the behavior with test mailboxes, created after Exchange 2013 has been installed into the organization. All these mailboxes can be migrated without password prompts.
By the way, I found different posts about the authentication settings for outlook anywhere. I found on Exchange 2007 that the ClientAuthenticationmode was Basic, while NTLM on Exchange 2013. So I changed it to NTLM as well. Everything is still working.
I am going to migrate 2 more mailboxes, and I will see tomorrow if the problem still exists.
Any Suggestion?
Regards
Peter

Hi Peter,
I also found many similar issues had been solved by setting to NTLM for Servers. Outlook will pass the authentication via Windows. It is the solution.
Thanks
Mavis
Mavis Huang
TechNet Community Support

Outlook 2011 for Mac with Microsoft Exchange 2007/2010

Hi,
For already a fews days I am troubleshooting a Mac Outlook 2011 <> Exchange sync issue. I've got exact the same symptoms in two totally different environments.
- Environment one:
Exchange 2007 SP3 RU 14 (8.3.379.2)
Outlook 2011 14.4.7
- Environment two:
Exchange 2010 SP1 RU 8 (14.1.438.0)
Outlook 2011 14.4.7
Problem:
Autodiscover and EWS synchronisation test from Microsoft Exchange Connectivity Analyzer is succesfull. Configuring an new (Exchange) e-mail account with Outlook2007/2010/2013 fully based on autodiscover works with no errors.
Configure Outlook 2011 based on autodiscover when connected to the internal LAN works. Configure Outlook 2011 based on autodiscover or by hand doesn't work from WAN.
I am unable to synchronize Outlook 2011 with Exchange when WAN connected (No error in logging). I am able to synchronize OS X Mail (Default OSX Mail client) with the same Exchange server.
Conclusion: the autodiscover function that Outlook 2011 uses does not work from WAN, the autodiscover function that Outlook 2007/2010/2013 and Exchange Connectivity Analyzer is using does work from WAN. Do I need to configure something special for synchronization
with Outlook 2011 other than explained above when working from WAN?
When testing EWS with 3th party tooling(EWS Editor) and Exchange Connectivity Analyzer everything is working as it should be. (all mailbox data is shown). If you need any more information about the context I am happy to provide.
Regards,
Mikkie van Falier

Hey hpujary.
Welcome to the BlackBerry Support Community Forums.
At this time, only contacts can be synchronized with BlackBerry Link software and a BlackBerry 10 Smartphones. The functionality to provide more options for PIM synchronization may be added in the future. I cannot say for certain that the issue outlined in KB27248 is resolved for BlackBerry 10 Smartphones as the functionality does not exist to confirm.
Cheers.
-Sawks
Come follow your BlackBerry Technical Team on Twitter !@BlackBerryHelp
Be sure to click Like! for those who have helped you.
Click Accept as Solution for posts that have solved your issue(s)

My Outlook prompts for password every time it comes back from sleep or started

I've Microsot Outlook for MAC 2011, version 14.4.1 installed on my MAC Book Pro Retina Display with OS X Version 10.9.2 and everytime my outlook comes back from sleep or is started or there is a little fluctuation in Wifi signals, prompts me for my email password. I checked the option of save my passord, deleted all previous passwords from Keychain but it doesn't works, so please help. My email at my official domain (not free domains) address is configured perfectly and my send and received is working fine.

I have that problem in Outlook, too. When I get the Yes/No dialog box, I simply click "No" and my machine continues to receive mail.
It's most certainly a pain, but coming out of sleep, your network doesn't kick in for a minute or two. I don't think that it's really a bug in either OS X or Outlook: it just takes that minute or so for the network to wake up.
Clinton

Internally installed Outlook 2010 prompts for password using external smtp email as user id

Hi,
After exchange 2007 to exchange 2013 migration all internally connected outlooks 2010 (xp, vista, win7, win8) prompt for password using external email user address as user id.
Below some of my settings and informations.
Internal domain: contoso.local
External domain: contoso.com
Exchange is NOT published to Internet at all.
Internally OWA, ECP runs OK.
Test-OutlookWebservices with user.name(at)contoso.local or contoso\user.name - runs OK
Test-OutlookWebservices with user.name(at)contoso.com - fails
Common scenario - (all happens internally):
1.User starts Outlook
2.Outlook prompts for password with default user.name(at)contoso.com as id
- while user tries to authenticate using his domain password - outlook re-prompts
- while user changes id from user.name(at)contoso.com to user.name(at)contoso.local or contoso\user.name and authenticates - Outlook connets to exchange and till next Outlook it runs ok.
I am bus with that issue since 1 week and I am already bit tired. I was looking for answer via gogle/bing and went through tons of "Outlook perpetually prompts for password" threads and blogs. No success.
Do you have any clue where else start to play with that?

Hi,
Thank you for answer - no luck
>NExt og to Connection tab - Exchange Proxy settings - Proxy authentication settings - is it set
>to NTLM or Basic?Give it a try on one of them.(if set to NTLM change to basic and vise versa).
On both settings the same results - Outlook is prompting for password.
>Another thing you could try is og to Internet Explorer - tool -internet options- Security - click local
>intranet - >custom Level and scroll Down to bottom and put check mark on automaticly logon
>With current username >and password.
>Do this on Trusted sites as well,if Your domain is listed under trusted sites
The same results - Outlook isprompting for password.
Should not be some kind of mapping set somehow in AD between user.name(at)contoso.com and user.name(at)contoso.local?
I have impresion that issue is somewhere in the fact that outlook is trying to connect using contoso.com instead of contoso.local in ntlm credentials.

Firefox keeps prompting me for password with the popup

Firefox at my work computer keeps prompting for password with the popup message "The proxy moz-proxy://proxy:9119 is requesting a username and password. The site says: "moz-proxy://proxy:9119"" This happens too often,even If i provide the username and password I get the next popup with same message.
Its very annoying, I am not finding web better because of this, I goggled and figured about the config settings of - network.automatic-ntlm-auth.allow-proxies and the other one not working.
I guess I am missing the PAC URL or something which I remember like solved the problem sometime back but not in same domain though.
Can someone help ?
Can the good community help ?

Quitting Calendar Agent is not working for me. I still get the following errors.
About 50 of these: 8/13/12 10:19:28.210 AM CalendarAgent[12480]: Unexpected EOF, returning last token as fallback
Then about 10 of these:
8/13/12 10:19:31.193 AM CalendarAgent[12480]: [com.apple.calendar.store.log.caldav.queue] [Account refresh failed with error: Error Domain=CoreDAVHTTPStatusErrorDomain Code=401 "The operation couldn’t be completed. (CoreDAVHTTPStatusErrorDomain error 401.)" UserInfo=0x7fb603b9d990 {AccountName=, CalDAVErrFromRefresh=YES, CoreDAVHTTPHeaders=<CFBasicHash 0x7fb603f5a4b0 [0x7fff79a05190]>{type = immutable dict, count = 10,
entries =>
    0 : Case Insensitive Key: X-Content-Type-Options = <CFString 0x7fb6038d0650 [0x7fff79a05190]>{contents = "nosniff"}
    1 : Case Insensitive Key: Content-Type = <CFString 0x7fb603bd3930 [0x7fff79a05190]>{contents = "text/html; charset=UTF-8"}
    2 : Case Insensitive Key: Server = <CFString 0x7fb603b1c400 [0x7fff79a05190]>{contents = "GSE"}
    3 : Case Insensitive Key: Transfer-Encoding = <CFString 0x7fff792226b8 [0x7fff79a05190]>{contents = "Identity"}
    6 : Case Insensitive Key: Date = <CFString 0x7fb603bf6300 [0x7fff79a05190]>{contents = "Mon, 13 Aug 2012 14:19:31 GMT"}
    7 : Case Insensitive Key: X-Frame-Options = <CFString 0x7fb603869680 [0x7fff79a05190]>{contents = "SAMEORIGIN"}
    8 : Case Insensitive Key: X-XSS-Protection = <CFString 0x7fb603b01740 [0x7fff79a05190]>{contents = "1; mode=block"}
    9 : Case Insensitive Key: Www-Authenticate = <CFString 0x7fb603bcf200 [0x7fff79a05190]>{contents = "BASIC realm="Google CalDAV""}
    11 : Case Insensitive Key: Cache-Control = <CFString 0x7fb603b08d50 [0x7fff79a05190]>{contents = "private, max-age=0"}
    12 : Case Insensitive Key: Expires = <CFString 0x7fb603bf8a20 [0x7fff79a05190]>{contents = "Mon, 13 Aug 2012 14:19:31 GMT"}

Outlook 2013 continually prompting for credentials on new domain

Greetings,
I first posted this in the Office365 community forums and was directed here.
We are experiencing an issue where Outlook 2013 (Office365 install) is prompting for user credentials every time it is opened, despite checking the option to remember the credentials. So far we've tried a number of troubleshooting steps, but nothing
has resolved the issue. The issue is happening to multiple users on multiple computers.
We are running:
Outlook 2013 (32-bit) (Office 365 install)
Windows 7.1 Professional (x64)
Computer is domain joined (Server 2012 R2 Domain Controllers)
Mail is hosted on Office 365
We've tried:
Clearing the Outlook and Office credentials from Credential Manager.
Removing the mail profile and the saved credentials from Credential Manager, then re-adding the mail profile.
We've tried adding the mail profile with both a manual configuration of the server settings and allowing Outlook to automatically configure them.
Ensuring that "Always prompt for logon credentials" is unchecked.
Setting "Always prompt for logon credentials" to disabled via registry (see
http://support.microsoft.com/kb/2984912)
Confirming that Autodiscover is able to connect (http://www.microsoft.com/en-us/showcase/details.aspx?uuid=e8db028a-06f4-45fb-aff1-e8ac896d29c5)
Deleting the Autodiscover.xml file so that it is recreated
Doing an Online Repair of Office 365.
Reinstalling Office 365
Recreating the user's Windows profile.
Ensuring all applicable Windows updates and Office updates are installed.
Changing Proxy Authentication from Basic to NTLM (will not connect with NTLM)
The machines this is occurring on are on a new domain that we are in the process of setting up. The user accounts are still on the old domain. Cross-domain trusts are set up in both directions and all other services are working fine. GPO settings across
both domains have been set up to be identical. The issue occurs on computers that were built directly on the new domain as well as computers built on old domain and migrated over. Machines that are not domain joined or are still on the old domain are not experiencing
the issue.
If any of you could provide any insight or other steps that we could try I'd greatly appreciate it.
Thanks

Hi,
For the issue that Outlook keeps prompting for password, I usually suggest users follow the steps in this article below, but apparently you have tried almost all the steps:
Why does Outlook keep prompting for password
I've seen some similar issues that were caused by an old "network driver", which for some reason caused a wrong server name to propagate up from the network layer to the application layer. Updating the network driver would fix the issue, I'm
not sure if this works in your scenario though.
Regards,
Melon Chen
TechNet Community Support
It's recommended to download and install
Configuration Analyzer Tool (OffCAT), which is developed by Microsoft Support teams. Once the tool is installed, you can run it at any time to scan for hundreds of known issues in Office
programs. Please remember to mark the replies as answers if they help, and unmark the answers if they provide no help. If you have feedback for TechNet Support, contact
[email protected]

Why does Outlook keep prompting for password

We have seen our community members ask questions about Outlook keeps prompting for credentials many times. This issue could be caused by numerous reasons. Below is a list of the most common reasons for this problem:
Outlook is configured to prompt you for credentials
Incorrect password cached in credential storage
Required Authentication Settings for outgoing server and incoming server
Outlook Anywhere is not configured to use NTLM Authentication
Corrupt Outlook profile
Slow or unstable network connection
Antivirus programs
Shared calendars
Outlook is configured to prompt you for credentials
If you are using an Exchange account, there is a setting in your Outlook profile to always prompt for logon credentials. To find the setting, please follow:
1. In Outlook 213, go to File tab > Info >
Account Settings > Account Settings…
2. Highlight your Exchange account and click Change button.
3. Click on More Settings button.
4. Select the Security tab.
5. Under the User Identification, make sure the “Always prompt for logon credentials” option is not selected.
If you are using other types of email, please make sure you have ticked the option “Remember password”.
Incorrect credential cached in Credential Manager
Your Windows system stores user credentials on your computer. If the cached credentials are incorrect, you will be prompted for password. This issue usually happens after the password for your domain user account is changed. Before your password changed,
you saved your credentials. The stored credentials are not overwritten when Outlook triggers the authentication prompt even if you enable the Remember my credentials option.
To fix this issue, you need to remove the corrupted credentials, follow these steps:
Click Start, click Control Panel, and then click Credential Manager.
Note If View by is set to Category, click User Accounts first, and then click Credential Manager.
Locate the set of credentials that has Outlook in the name.
Click the name to expand the set of credentials, and then click Remove from Vault.
Repeat step 3 for any additional sets of credentials that have the word Outlook in the name.
Required Authentication Settings for outgoing server and incoming server
Different email provider may need different authentication settings. Please make sure you have set the server settings correctly. You can contact your email provider to gather the information.
In general, we select the “My outgoing server (SMTP) requires authentication” option and the first bullet “Use same settings as my incoming mail server”.
In addition, click on the Advanced tab and check if you have enter the correct Server Port Number and select the correct encrypt type. Below is a screenshot for an IMAP account:
Outlook Anywhere is not configured to use NTLM Authentication
The Outlook Anywhere feature allows you to access your Exchange account remotely from the Internet when you are working outside your organization's firewall.
When using Outlook Anywhere to connect to your Exchange server, we need to choose
the authentication method among Basic Authentication, NTLM Authentication and Negotiate Authentication. The difference among them is the way that the passwords are sent when connecting to the server. With Basic Authentication,
the password is sent in clear text. Using NTLM Authenticationcan significantly reduce the number of password prompts.
To check the authentication setting, please go to File > Account Settings > Account Settings,
select the Exchange account, and then click
Change. In the Change Account wizard, click
More Settings, and then click the Connection tab. Click the Exchange Proxy Settings button and now, you can see the settings under
Proxy authentication settings. Try to change the authentication to
NTLM Authentication and then check the issue again.
Slow or unstable network connection
If your network connection is slow or unstable, Outlook may lose connection to the mail server. When Outlook try to reconnect, it will prompt for the credentials. To verify this, please switch to a stable network environment and then check if this issue
persists.
Corrupt Outlook Profile
Corrupt profile may cause Outlook to no longer remember your password. Please try to create a new mail profile in Control Panel and reconfigure your email account in the new profile to fix the issue. To create a new mail profile, you can refer:
http://support.microsoft.com/kb/829918
Antivirus software
Antivirus software usually integrates into your Outlook and it may cause some conflicts. Try to temporarily turn off your antivirus software to check if the issue will be gone.
Shared Calendar
Shared calendars can impact the user credentials, this issue may also occur if you have shared calendars opened in Outlook. You can try to unselect the shared calendar to check the result. It’s recommended to not open the shared calendar unless you want
to view them.
If you have any comments, welcome to post in the forum. Thank you.
Please click to vote if the post helps you. This can be beneficial to other community members reading the thread.

Nope...
I went through point by point by point, top to bottom, checking and verifying every single item as a possible cause for why my system (Outlook 2013 running on Windows 8.1 and connecting to Exchange 2010) insists on prompting me for my password every single
time I start Outlook. None of the solutions worked, my system still prompts me. I don't even have to supply a password. When the prompt dialog appears, I just cancel it. Within a few seconds, the bottom Outlook status bar changes to
"Need Password" with a key icon to the left. Then I just click on that message and immediately Outlook connects to Exchange.
The freaking software is BROKEN! Period.

Outlook 2010 prompting for password

Hi everybody. I ran into an issue yesterday morning where at one of our sites Outlook 2010 has started prompting for a username and password. If the user types in their username as "MYDOMAIN\myuser" and their password, it lets them in but the Exchange
status shows as "Disconnected". If the user sets their username to just "myuser" without the domain on the front it lets them in and works as expected until they close Outlook, at which point they have to enter their credentials again.
The strangest thing about this is that it's only affecting one of our sites and only Outlook 2010. Users running 2007 and 2003 do not have the problem and only users at this physical location have the problem. Does anybody know where I can look? I have tried
clearing stored credentials, created new Outlook profiles and reset passwords. None of these things seem to have had any effect.

After changing a ton of outlook settings, deleting the user's account profile on outlook, deleting their domain profile from the effected computer, trying to fix the registry, deleting stored credentials, etc.... almost everything else I found something
that FINALLY worked for me after over a year and about 12 different users being effected.
in the past I would just give up after much frustration and upgrade them to Office 2013 but that gets very expensive especially when I have 57 other users that could potentially run into the same issue.
Here is what I did.
- back up the user's data. log out and log into local admin
- delete the user from the local registry
- repair Office 2010 through control panel/programs, restart
- have user log back in with their credentials to make new local profile. recover their backed up documents. log out and log back in as local admin.
- install hotfix KB2597011
- restart computer
- install hotfix KB2583935
-restart computer
- log in, open outlook and setup user's account.
Some of these steps may be skipped as I didn't find the hot-fixes until after I repaired office, however I am just providing what I did in the process to end up with a working outlook again.
Some things unique to my situation that may or may not help.
- I noticed some of the computers have Office2010 32bit installed on 64 bit machines.
- Some of the users were swapped over using a profile mover program when we moved to a domain environment.
- For me this always happens when the user's passwords expire and they have to log in to the portal to change it. Then outlook starts with the repeated prompt for passwords. It is always computer specific and nothing but what I provided above has worked
other than re installing windows 7 and then office or upgrading to office 2013.

Outlook 2007 Clients Prompt For Password When Opening

I am running Exchange 2007 Standard. New outlook 07 clients prompt for password each time it is opened. Older clients do not prompt for password. Is there any way for outlook 07 to not prompt for password? Users already logged into domain, should their credentials not be recognized automatically like with outlook 03?

This fixed it for me.
http://social.technet.microsoft.com/Forums/en-US/exchangesvrgeneral/thread/383d130e-869f-4fce-9502-8b340904b0ba/#636c5a5e-c61f-414b-8e85-562c888b83cc
Quote:
Same problem here after restarting SBS 2008 for upgrades (annoying login box popping up after starting Outlook and also other times).
This solved the problem for me:
IIS Mgr on SBS 2008 / - / SBS Web Applications /
- SSL Settings / Client certificates - Stop / Start web server after changing settings:
Autodiscover: Ignore
EWS: Ignore
OAB: Accept *)
owa: Accept *)
Rpc: Accept *)
RpcWithCert: Accept *)
*) All these have to be Accept to get rid of login box
Best regards
Bjorn
I was having the same issue. SBS2008, Exchange 2007. Only being prompted in Outlook 2007 clients. Tried a lot of different things to fix it, but none worked. This started happening after a round of security updates but I could not find KB2412171 on the list.

Problem with Fresh/New Exchange 2013 - Exchange Account, Unable to verify account information

hi!
For a client, i just setup AD (windows 2012 R2), and Exchange 2013 installed on Windows 2012 R2.
The AD is brand new, the exchange is installed correctly, i setup send connectors, and i could send and receive emails succefully.
But, when i want to use mobile devices like iphone, i receive the error as in title.
I've not changed anything from the default policies of Mobile devices policy...
What could be the problem?
how can i fix?
Regards!
Lasandro Lopez

Hi Lasandro,
Agree with Dare, Exchange 2013 is not supported to run on Windows Server 2012 R2.
Exchange 2013 SP1 will add Windows Server 2012 R2 as a supported operating system for Exchange Server 2013 with SP1.
For more information, here is a blog for your reference.
Exchange Server 2013 Service Pack 1 Coming in Early 2014
http://blogs.technet.com/b/exchange/archive/2013/11/20/exchange-server-2013-service-pack-1-coming-in-early-2014.aspx
Hope it helps.
Best regards,
Amy
Amy Wang
TechNet Community Support

Outlook 2010 keeps prompting for password

Hi,
We use Exchange 2008 and Outlook 2010. For some reason, Outlook 2010 keeps prompting for password. My use entered the password and checked "Remember Password" box, but next morning when he logged in, he still got the prompt.
I removed the Outlook credential for Outlook listed under Password Credential in Control Panel, but still no help.
Please advise!
Thanks in advance!
Grace

Hi Grace
1. Open Outlook 2010. Click File>Account Settings>Account Settings.
2. Click the E-mail tab, click the Exchange Online mailbox, click Change…
3. Click More Settings…. Click the Security tab, make sure the Always prompt for logon credentials box is unchecked.
Please mark it answer if it helps you solving your problem
Amit Kotha

Outlook prompting for password with new Exchange 2013

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