We Are Temporarily Unable to Process Your Request You Can Try Again in a New Session Adp
Authentication prompts in Outlook is one of the worst to troubleshoot in a Messaging Environment. Only if your clear about your Compages and the connectivity flow it could be much easier for yous to isolate the event. I have listed the virtually mutual scenarios . Lets run into one by 1.
- Microsoft Function Patches
- Understanding Outlook Behaviour and Credential Manager`with HTTP MAPI
- Proxy Exclusions
- Hardware Load Balancers
- Custom Outlook Add-ins
- Conflicting Outlook Anywhere Settings in Co-existence Surround.
- Public Folders Co-existence not configured Properly.
- Additional Mailboxes
- SSL misconfiguration
- Customized Virtual directory authentication settings
- Autodiscover Asking failure
- Offline Address Books
- Outlook Integration similar Instant Messaging
- Active Directory Replication
- Principal Email Accost and User Principal Name Mismatch in Office 365 Hybrid
Microsoft Office Patches –
I know Microsoft patches are crazy sometimes . But i strongly recommend to upgrade the Microsoft Office to the latest version to stay secured besides so that you don't work on a event which is already fixed. There are many feature optimizations and Protocol enhancements fabricated over these months . And so before fifty-fifty start troubleshooting make sure you have the latest version of Function running . So that it helps yous to isolate the issue faster and quicker.
Understanding Outlook Behaviour and Credential Manager`with HTTP MAPI –
when we are using RPC HTTP information technology wasn't mandatory to store credentials on the local machine. But hither comes the HTTP MAPI where it makes it mandatory for users to store the countersign in the credential director when the users leave the domain network.
As of today when a domain joined machine leaves the domain / corporate / internal network and goes external. Outlook Prompts for credential to enter it once to store in the credential manager. So that it won't ask you again. Until the countersign expires on it. This wasn't the case or behaviour with RPC HTTP.
Seeing Connectedness Condition in Outlook shows you. The Outlook is using RPC HTTP or HTTP MAPI.
Note : Office 365 / Exchange Server 2016 uses HTTP MAPI as default
when the user stores the credential . Yous can see them every bit
MicrosoftOffice16_DataSSPI:user@domain.com in the Windows Credential Manager
If user checks : Remember Countersign It shows as Enterprise. It means its going to enquire again until the password expires from the External Network
If user doesn't check Recollect Password information technology will show as Logon Session . It means when user logs of and logs in . Credential are stored just for the logon session and it will prompt the user when the user is on the external network
Seeing in the Control Panel Credential Manager – Remembering Credentials
Seeing in the Control Panel _ Credential Manager without remembering the credentials
MicrosoftOffice16_DataSSPI:user@domain.com
Logon Session
this behavior is by design when user is on the External Network for Substitution Server 2016 .
Proxy Exclusions –
Proxy Exclusions play a major office when information technology comes to credential prompts . Lets see the near seen consequence is using a PAC file
if your using a pac file , Outlook may fail with Authn "Fault" in connexion status
Sample Proxy Settings on Pac File – http://pac.zscloud.net/azure365pro.pac
If your using On Premises you lot arrive to featherbed the traffic and become direct. So that when they are in Domain it goes to the Commutation Server Directly.
Sample –
if you using Substitution Online – Its preferred to go via proxy and yous will not fix directly settings on pac file. Brand certain all Function 365 Urls are excluded from the proxy. For Example zscaler gives One Click Configuration for Part 365
Hardware Load Balancers –
ByPassing Hardware load balancers is more than important as Outlook loses session persistence , Load balancer may requite out the request to a different exchange server every fourth dimension information technology connects. So near of the fourth dimension it could be a configuration issue. Equally we cannot become into details of those issues . As its wide telescopic. Simply to make sure its not a load balancer issue. Make a host file pointing to the Commutation Server encounter if you are experiencing the same outcome which can answer yous many things
I have documented the steps on F5 if you utilise one https://www.azure365pro.com/configure-f5-ltm-exchange-server-2016/
Custom Outlook Add together-ins –
There are many Add-ins for Outlook . Which may crusade credential prompts. Outlook Safe mode can respond you those. Safe mode removes all the Addins on start up temporarily for you to test the behaviour of Outlook to isolate the aforementioned issue.
Conflicting Outlook Anywhere Settings in Co-existence Environment –
Credential prompts may exist a reason when they are not able to proxy into the destination server. Where Outlook anywhere wasn't mandatory in environments . When it comes to Exchange Server 2016 . Outlook anywhere has to be enabled on all Exchange 2010 servers for instance . when you want to start with an co-existence. Outlook anywhere settings has to match betwixt the legacy servers and the new exchange servers when you setup a coexistence . In lodge to have shine client connectivity.
In my case . In my contempo migrations – Commutation Server 2010 was fix to use NTLM . so made the aforementioned configuration on Exchange 2016 then the co-beingness connectivity was successful.
In one case the Co-existence period is over . we have put back recommended settings on Substitution Server 2016 having them to use negotiate
Basic authentication: If you select this authentication type, Outlook will prompt for username and password while attempting a connection with Exchange.
NTLM authentication: If you select this authentication type, exchange does not prompt users for a user proper name and password. The current Windows user information on the client computer is supplied past the browser through a cryptographic commutation involving hashing with the Web server. If the authentication exchange initially fails to place the user, the browser will prompt the user for a Windows user business relationship user name and countersign. And so, when Outlook is trying to connect to Exchange and if the machine is domain joined, there isn't a need to provide password.
Negotiate authentication: Enabled by default in Exchange 2013. This is a combination of Windows integrated authentication and Kerberos authentication. If nosotros employ negotiate hallmark, exchange volition authenticate the client using NTLM authentication blazon and if unable to verify authenticity, will claiming the client to cosign using a username and password.
Equally explained these Outlook anywhere settings are not matching between the legacy servers and the new prompts . There are more chances of getting Intermittent Outlook prompts
Public Folders Co-existence non configured Properly –
If you have Exchange 2016 and Exchange 2010 in your environment. Outlook may prompt or slow it down to connect when its not able to reach the public folders of Exchange 2010 via Exchange 2016.
In our example we have decided to remove Default Public Folder Database as nosotros are not planning to migrate it to the new system.
Cleared using msExchHomePublicMDB aspect on Commutation 2010 Database
Start – run – adsiedit.msc – Configuration sectionalization
CN=Services -> CN=Microsoft Substitution -> CN=(your organization name) -> CN=Administrative Groups -> CN=Exchange Administrative Group (FYDIBOHF23SPDLT) -> CN=Databases.
- msExchHomePublicMDB
Now make sure Outlook is not trying to reach Commutation 2010 or legacy server public folders , You lot tin always see the Outlook Connectedness status to cheque the same.
or you can attempt to setup co-existence https://technet.microsoft.com/en-united states/library/dn690134(v=exchg.150).aspx
Additional Mailboxes –
Make sure Outlook is not configured with additional mailboxes . As sometime the primary mailbox may be on the new version and the additional mailbox is yet on the legacy servers or vice versa which may crusade prompts. Y'all can always remove them and bank check it ,
SSL misconfiguration –
SSL misconfigurations like
- Wrong Entries on Go-OutlookProvider
- Unsupported wild carte du jour certs.
Customized Virtual directory authentication settings –
There could be change in Authentication settings. Listed Exchange 2016 default authentication settings on virtual directories from a healthy environment.
MAPI –
EWS –
OAB –
RPC –
Backend Site bindings –
MAPI _ Backend
EWS _ Backend
OAB _ Backend
Autodiscover Asking failure –
Hold Ctrl key and right click on outlook icon on the task bar. examination e-mail configuration run autodiscover. verify its returning correct urls in a timely style.
Offline Accost Books –
Make sure Offline Address Book assigned properly on Databases.
Make sure Outlook tin can download Offline Address books properly from the client side.
Instant Messaging Integration –
This prompt is one of the finest example where Cisco Jabber trying to get request information from Outlook before Outlook Connects to Exchange server. you can isolate the issue past only removing such products from startup
Master Email Address and User Primary Proper noun Mismatch in Office 365 Hybrid
When your email and User Primary Proper noun is not matching in Active Directory. You tin run into repeated Outlook authentication Prompts
Happy Hallmark Prompts .
Source: https://www.azure365pro.com/troubleshooting-authentication-prompts-in-outlook/
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