troubleshooting issues with outlook® connectivity

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Customer Service & Support Troubleshooting Issues with Outlook® Connectivity August 30, 2012

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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. - PowerPoint PPT Presentation

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Page 1: Troubleshooting Issues with  Outlook® Connectivity

Customer Service & Support

Troubleshooting Issues with Outlook® Connectivity

August 30, 2012

Page 2: Troubleshooting Issues with  Outlook® Connectivity

Customer Service & Support

Agenda How Outlook® Connectivity to Office 365 Works Troubleshooting Tools/Methods Scenarios

(Total time: 1 hour)

Page 3: Troubleshooting Issues with  Outlook® Connectivity

On Premises AD Forest

Exchange Online

Remote MailboxPrimary Smtp Address = [email protected] Routing Address = [email protected]

MailboxPrimary Smtp Address = [email protected] Smtp Address = [email protected]

Outlook Client

(1) Where is my mailbox?

(2) Local Exchange passes a redirect to “service.contoso.com”

(3) Outlook attempts to discover endpoint through DNS record “autodiscover.service.contoso.com”

(4) Request Authentication

(6) Profile Builds(5) Authentication Success

AutodiscoverOutlook Profile Generation

Page 4: Troubleshooting Issues with  Outlook® Connectivity

Customer Service & Support

Troubleshooting Tools/Methods Web Powershell Outlook® Networking Miscellaneous

Page 5: Troubleshooting Issues with  Outlook® Connectivity

Customer Service & Support

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

Page 6: Troubleshooting Issues with  Outlook® Connectivity

Customer Service & Support

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" ?> <Autodiscover xmlns="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>

Page 7: Troubleshooting Issues with  Outlook® Connectivity

Customer Service & Support

Powershell Get-CASMailbox

Determine if mailbox is enabled for MAPI Get-CASMailbox <user> | fl MapiEnabled

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> | fl UserPrincipalName,Guid Get-Mailbox <user> -SoftDeletedMailbox | fl UserPrincipalName,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

Page 8: Troubleshooting Issues with  Outlook® Connectivity

Customer Service & Support

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

Page 9: Troubleshooting Issues with  Outlook® Connectivity

Customer Service & Support

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.comPinging 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

Page 10: Troubleshooting Issues with  Outlook® Connectivity

Customer Service & Support

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

Page 11: Troubleshooting Issues with  Outlook® Connectivity

Customer Service & Support

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-MsolUser cmdlets to troubleshoot Example (Looking up specific user):

Get-Mailbox <user> | fl UserPrincipalName,Guid Get-Mailbox <user>-SoftDeletedMailbox | fl UserPrincipalName,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 ErrorCode of 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

Page 12: Troubleshooting Issues with  Outlook® Connectivity

Customer Service & Support

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