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Troubleshooting Issues with Outlook® Connectivity

Troubleshooting Issues with Outlook® Connectivity. August 30, 2012. Agenda. How Outlook® Connectivity to Office 365 W orks Troubleshooting Tools/Methods Scenarios (Total time: 1 hour). Autodiscover Outlook Profile Generation.

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Troubleshooting Issues with Outlook® Connectivity

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  1. Troubleshooting Issues with Outlook® Connectivity August 30, 2012

  2. Agenda • How Outlook® Connectivity to Office 365 Works • Troubleshooting Tools/Methods • Scenarios (Total time: 1 hour)

  3. AutodiscoverOutlook Profile Generation (3) Outlook attempts to discover endpoint through DNS record “autodiscover.service.contoso.com” (1) Where is my mailbox? (2) Local Exchange passes a redirect to “service.contoso.com” (4) Request Authentication (5) Authentication Success (6) Profile Builds

  4. Troubleshooting Tools/Methods • Web • Powershell • Outlook® • Networking • Miscellaneous

  5. Web • OWA • https://outlook.com/<domain> or via O365 portal(https://portal.microsoftonline.com) • Determine if user can log into their mailbox at all • Determine if user’s temporary password has been changed (must be changed before Outlook® can connect) • For non-Identity Federation configurations, if able to log in, it helps verify user credentials are ok/correct • ExRCA (Exchange Remote Connectivity Analyzer): • https://www.testexchangeconnectivity.com/ • “Outlook Autodiscover” & “Outlook Anywhere (RPC over HTTPS)” tests • Independent of client & network client is on • O365 portal: • https://portal.microsoftonline.com • Determine autodiscover CNAME record information for O365 domain • Determine if user has been blocked from signing into account • Another way to verify if user credentials are ok/correct (good test if OWA login fails) in non-Identity Federation (aka SSO) configurations • Take Exchange out of the picture

  6. Web (Cont’d) • O365 DIY Troubleshooting Tool: • http://community.office365.com/en-us/tools/troubleshooting.aspx • Helps narrow down & shows possible solutions for the issue • Recording Explaining Tool at http://community.office365.com/en-us/blogs/office_365_technical_blog/archive/2012/08/09/troubleshooting-issues-with-sending-and-receiving-email-in-office-365-lync-and-learn.aspx • Browser itself: • Example: https://autodiscover-s.outlook.com/autodiscover/autodiscover.xml • Prompted for Org ID credentials • Good response below: <?xml version="1.0" encoding="utf-8" ?> <Autodiscoverxmlns="http://schemas.microsoft.com/exchange/autodiscover/responseschema/2006"> <Response> <Error Time="00:38:55.0596225" Id="1018033456"> <ErrorCode>600</ErrorCode> <Message>Invalid Request</Message> <DebugData /> </Error> </Response> </Autodiscover>

  7. Powershell • Get-CASMailbox • Determine if mailbox is enabled for MAPI • Get-CASMailbox <user> | flMapiEnabled • For Outlook® to connect MapiEnabled must be set to True • How to correct: Set-CASMailbox <user> -MapiEnabled $True • Get-Mailbox/Get-MsolUser • Determine if “soft deleted” mailboxes with duplicate UserPrincipalName exists • Get-Mailbox <user> | flUserPrincipalName,Guid • Get-Mailbox <user> -SoftDeletedMailbox | flUserPrincipalName,Guid • Get-MsolUser–UserPrincipalName <user’s UPN> -ReturnDeletedUsers | fl • Test-MAPIConnectivity • Determine if mailbox can be accessed via MAPI: • Test-MAPIConnectivity <user> | fl • Good response: Result = Success • Bad response : Result = *FAILURE* • Error listed with bad responses

  8. Outlook • Test E-mail AutoConfiguration • Ctrl – Right-click on Outlook icon in system tray • Disable “Guessmart” check boxes • Autodiscover Log • Outlook Logging must be enabled via Outlook GUI or EnableLogging registry DWORD entry • http://support.microsoft.com/kb/831053 • Olkdisc.log file located in %temp% • Connection Status • Ctrl – Right-click on Outlook icon in system tray • Manual Configuration • Follow “Method 3: Manually set up Outlook” from http://support.microsoft.com/kb/2404385 • Tests MAPI connectivity to mailbox • Autodiscover, OOF/Availability, & OAB will still fail if Autodiscover was failing before

  9. Networking • Netmon/WireShark • Outlook traffic to O365 is encrypted (RPC over HTTPS), but you can look for retransmits and/or blocked packets • TCP port 443 must be allowed through networking devices • Look at DNS traffic for resolution attempts on autodiscover FQDNs • Example: autodiscover-s.outlook.com • Ping • Determine if autodiscover DNS record resolves • Example: C:\>ping autodiscover-s.outlook.com Pinging autodiscover-s.outlook.com [157.56.240.137] with 32 bytes of data: Request timed out. Etc… • NSLookup • Determine if autodiscover DNS record resolves • DNS • In split-brain DNS environments, autodiscover record must also be created on internal DNS servers

  10. Miscellaneous • MOSDL Support Toolkit • http://support.microsoft.com/kb/960625 • Performs network diagnostics and collects configuration and logging information • Example: NSLookup, ExRCA Outlook Anywhere test, etc… • Things to try • Working user on same client as affected user • Affected user on another client, including on a working user’s client • Affected user on a client on a different network

  11. Scenarios • Soft Deleted Mailboxes • http://support.microsoft.com/kb/2619308 • ExRCA“Outlook Anywhere” test shows “HTTP 401 Unauthorized” error when making Autodiscover XML request to https://pod51xxx.outlook.com/Autodiscover/Autodiscover.xml • Use Get-Mailbox & Get-MsolUsercmdlets to troubleshoot • Example (Looking up specific user): • Get-Mailbox <user> | flUserPrincipalName,Guid • Get-Mailbox <user>-SoftDeletedMailbox| flUserPrincipalName,Guid • Get-MsolUser–UserPrincipalName <user’s UPN> -ReturnDeletedUsers | fl • O365 license removed/re-added • OWA error shows “Your account has been disabled.” • ExRCA “Outlook Anywhere” test shows ErrorCodeof 500 with Message of “The e-mail address cannot be found.” when making Autodiscover XML request to https://pod51xxx.outlook.com/Autodiscover/Autodiscover.xml • Can take up to 24 hours before mailbox can be accessed

  12. Scenarios (Cont’d) • Sign-in Access Blocked • This is an intentional block on the user against any access, including Outlook® Anywhere • OWA and O365 portal shows error “Sign-in is blocked” • User must be allowed sign-in access via the O365 portal(Users -- <user> -- Settings –Set Sign-In Status = Allowed) • Password Reset/Expired • User has password reset (i.e. user has temp password) or it expires • “HTTP 456” error when making Autodiscover XML request to https://autodiscover-s.outlook.com/Autodiscover/Autodiscover.xml • User with temporary password must log into either O365 portal and/or directly into OWA and change their password • User with expired password must contact their admin/help desk to get a new temporary password and then change their password

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