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The art of troubleshooting Office 365 Agenda: Tool review Top Issue Review Resources

Troubleshooting Tools There are numerous troubleshooting tools you can use depending on the issue and product Knowing what tools to use and when will help you more quickly diagnose the issue The more information gathered will help drive traction with any escalation to Microsoft support.

Tools Matrix Technology Tool Office 365 Platform Admin center –various tools Office 365 DIY Troubleshooter (Demo) Exchange Online Exchange admin center –various tools Remote Connectivity Analyzer (Demo) SharePoint Online SharePoint Admin Center Lync Online Lync Admin Center - various tools Remote Connectivity Analyzer Transport Reliability IP Probe tool

Office 365 DIY troubleshooter Self-diagnosis tool, which any customer or user can run Contextual options based on the previous answer provided Links to articles to resolve the most common issues http://community.office365.com/en-us/p/troubleshooting.aspx Demo

Remote Connectivity Analyzer Web-based tool that can help diagnose any connectivity issues. In addition, RCA website offers tests for Microsoft Exchange ActiveSync, Exchange Web Services, Microsoft Office Outlook, Free/Busy, and Internet email. http://aka.ms/o365rca http://support.microsoft.com/kb/2650717 Demo

Top Issue Review #1 Troubleshooting Mail flow The first step in knowing how to troubleshoot mail delivery issues is to understand how mail flows. The path of mail flow will differ depending on whether the environment is an Office 365 (Cloud Only) user connection or a coexistence environment between on- premises and Exchange Online. #1 Troubleshooting Mail flow

Mail Flow Review Sending and receiving email involves many parts: The end-user’s computer and email settings Rules and Compliance The SMTP servers that receive and queue up the email for relay to the recipient’s domain server The DNS lookup for the recipient’s inbound mail server The spam filter The recipient’s domain servers The recipient’s email address When troubleshooting email, all of these factors must be taken into consideration to diagnose the issue. Exchange provides help in the form of non-delivery reports (NDRs)

Mail Flow Topology Instructor: Keep at a high level, this will be discussed in more depth later in this section. Comes directly to us Through 3rd party spam filter Or hybrid through your on premise

Message Traces Message Traces are generated by Administrators in EAC > Mail Flow > Message trace Provide intimate detail on where a message is up to from Exchange Online point of view Supports searching using any arbitrary email address (inbound or outbound) Provides all recorded instances of inbound or outbound email that has been exposed to Exchange Online transport pipeline Message Trace is a part of Exchange Online Protection (EOP).

Message Trace Example 6/21/2013 3:18:54 AM FAIL The message was not delivered. Two days later the outcome was: “6/21/2013 3:18:54 AM FAIL The message was not delivered. “ and an NDR was generated and returned to the sender.

Top Issue Review #2 Mail delivery issues What Is an NDR? An NDR is an email message returned to the sender to notify the sender that the mail did not reach the recipient. NDRs are generated either by the SMTP server on the sender’s side or the Exchange Server on the receiver’s side, depending on the issue. Not all servers use the same NDR formats Not all scenarios produce NDRs “Smoking Gun” of diagnostic information for failed email delivery #2 Mail delivery issues Common causes of email connection problems DNS records for your organization aren’t set up. An MX record is required to receive email. A CNAME Autodiscover record is required to allow connections through Outlook. An SPF record lets other organizations know your email came from a trusted source. DNS records for your organization need to be changed. If your organization was recently migrated or received a service update, you may need to update your DNS records. Outlook profiles are set up to use a specific server name instead of using Autodiscover. We need to be able to move mailboxes around for datacenter maintenance and service updates, so use of Autodiscover is required by your organization to make sure we don’t break things for you. Unsupported version of Outlook. The version of Outlook that you are using has to meet Office 365 requirements and should also have all of the latest updates applied. We recommend using Windows Update so that your version of Outlook always has the latest software updates. http://community.office365.com/en-us/wikis/solutions/fix-email-connection-problems.aspx

NDR Diagnostic Evaluation Diagnostic information should be read from bottom to top. The significant information that is included is as follows: Generating server: the server that sends the NDR Enhanced Status Code: the code that defines the reason for the error and points to possible causes Time between servers, known as Hop delays, that may signal latency or connectivity issues The message on the next slide shows the following: The message was sent on April 6, at 10:23:36 (EDT), and the NDR was returned on April 6, at 14:24:35 (PDT) or 10:24:25 EDT, for a total time of 49 seconds. Diagnostic Information for Administrators Section The Diagnostic information for administrators section contains more detailed information about the specific error that occurred during delivery of the message, the server that generated the NDR, and the server that rejected the message. The following fields are present in most NDRs and are visible in the "NDR sections" figure earlier in this topic: Generating server   The generating server is the Exchange 2007 server that created the NDR. The generating server takes the enhanced status code that is explained later in this topic. This code creates an easy-to-read NDR. If no remote server is listed below the e-mail address of the sender later in the Diagnostic information for administrators section, the generating server is also the server that rejected the original e-mail message. If message delivery fails when the message is sent to another recipient in the same Exchange 2007 organization, the same server typically rejects the original message and generates the NDR. Rejected recipient   The rejected recipient is the e-mail address of the recipient to which delivery of the original message failed. If delivery to more than one recipient has failed, the e-mail address for each recipient is listed here. The rejected recipient field also contains the following sub-fields for each e-mail address listed: Remote server   The remote server field contains the FQDN of the server that rejects delivery of the message during the Simple Mail Transfer Protocol (SMTP) conversation. The remote server field is only populated when delivery has been attempted to a remote server, and that delivery attempt has been rejected before the receiving server successfully acknowledges the message after the message body is sent. If the original message is successfully acknowledged by the receiving server and is then rejected because of content restrictions, for example, the remote server field is not populated. Enhanced status code   The enhanced status code is the code returned by the server that rejected the original message. The enhanced status code indicates why the original message was rejected. The enhanced status code is not rewritten by Exchange 2007 but is used to determine what text to display in the user information section. The enhanced status codes you're most likely to encounter are listed in "Common Enhanced Status Codes" later in this topic. For a detailed list of enhanced status codes, see RFC 3463. SMTP response   The SMTP response is the machine readable text returned by the server that rejected the original message. The SMTP response typically contains a short string that provides an explanation of the enhanced status code that is also returned. The SMTP response is not rewritten by Exchange 2007. And this response is always presented in US-ASCII. Original message headers   The original message headers section contains the message headers of the rejected message. These headers can provide useful diagnostic information, such as information that can help you determine the path that the message took before it was rejected or whether the To field matches the e-mail address that is specified in the rejected recipient field. http://technet.microsoft.com/en-us/library/bb232118(v=exchg.141).aspx http://technet.microsoft.com/en-us/library/bb232118(v=EXCHG.80).aspx

Diagnostic Info Example Diagnostic information for administrators: Generating server: contoso.com tony@contoso.com cdptpa-contoso.mail.com #550 5.1.1 - Invalid mailbox: tony@contoso.com ## The message was sent on April 6, at 10:23:36 (EDT), and the NDR was returned on April 6, at 14:24:35 (PDT) or 10:24:25 EDT, for a total time of 49 seconds.

User Information Example NDR User information gives feedback to the sender that the email was not delivered. In some instances, it gives the reason so that the sender can modify the outgoing email. _____________________________________________ Delivery has failed to these recipients or distribution lists: tony@contoso.com The recipient's email address was not found in the recipient's email system. Microsoft Exchange will not try to redeliver this message for you. Please check the email address and try resending this message, or provide the following diagnostic text to your system administrator. The following organization rejected your message: contoso.mail.com. Sent by Microsoft Exchange Server 2010 SP1 ________________________________________________ User Information Section The user information section of an NDR generated by Exchange 2007 contains information that you want to communicate to an end-user who has sent a message that is later returned with an NDR. The text that is displayed in this section is inserted by the computer that is running Exchange 2007 that generated the NDR. The text in the user information section is designed to help the end-user determine why the message was rejected and how to resend the message successfully if the message should be resent. When applicable, the fully qualified domain name (FQDN) of the server that rejected the message is included in the user information section. If delivery fails to more than one recipient, the e-mail address of each recipient is listed and the reason for the failure is included in the space below the recipient's e-mail address. http://technet.microsoft.com/en-us/library/bb232118(v=exchg.141).aspx http://technet.microsoft.com/en-us/library/bb232118(v=EXCHG.80).aspx

What Do Error Codes Mean? Error codes that indicate a persistent transient failure begin with a 4. Error codes that indicate a permanent failure begin with a 5. Some common error codes are as follows: Issues on the sender side: 5.1.1: Bad destination. This typically occurs when the sender misspells the recipient’s address or uses the auto- complete function after an email address has changed. 5.2.3: Message too large. The outgoing message, usually because of attachments, exceeds the limit set by the Exchange administrator. Domain server issues: 5.0.0: HELO/EHLO requires a domain address. SMTP commands are sent back and forth between the sending and receiving server. When the sending server does not receive a response, this error code is generated. Issues on the receiver side: 5.2.2: Mailbox full–recipient has exceeded the storage quota. http://technet.microsoft.com/en-us/library/bb232118(v=exchg.141).aspx http://technet.microsoft.com/en-us/library/bb232118(v=EXCHG.80).aspx

Delivery Reports Email sent to another mail system Delivery Report for tom@tailspintoys.com (tom@tailspintoys.com) Submitted 19/06/2013 10:23 AM The message was submitted. Transferred 19/06/2013 10:23 AM The message was successfully handed off to a different email system. This is as far as we can track it. Email sent to another mail system Submitted 19/06/2013 10:29 AM The message was submitted. Pending 19/06/2013 10:32 AM This message is traveling normally. For an update, check back in a few minutes. Sent but no MX Record for destination* 19/06/2013 12:46 PM Message delivery is taking longer than expected. There may be system delays. For more information, contact your helpdesk. Sent but no MX Record – two hours later Delivery Report for Amy Alberts ‎(amya@ContosoT3.onmicrosoft.com)‎ 19/06/2013 10:33 AM Delivered The message was successfully delivered. Email sent internally and verified received Failed 6/21/2013 10:32 AM The message couldn't be delivered. Sent but no MX Record – two days later An NDR will be returned by the internal Exchange service at this stage. All Exchange can report is that the message is out side of its reporting boundary since it is now the processing responsibility of the other mail system. NDRs, if any, will have to be returned by the other mail system. Since the recipient is internally handled by the same mail system. Delivery can be confirmed. Message stays in pipeline and retries for 48 hours * This scenario applies in many circumstances where the destination mail server is unresponsive. Service acknowledges delay

Message Trace & Delivery Reports Accessed by Administrators only Admins and Users Search Scope Any arbitrary email address Only existing mailboxes Detail Level Pipeline Events and Server information Summary of when sent and final outcome if available Best used by Administrators Users Main use scenario Diagnostics and Troubleshooting Business agenda / policy - confirming delivery Message Traces are generated by Administrators in: > EAC > mail Flow > message trace for any user Delivery Reports can be generated by end users using: > OWA > options > organize email > delivery reports for only their respective mailboxes Delivery Reports can be generated by Administrators using: > EAC > mail flow > delivery reports for any user It is often useful for administrators to use Delivery Reports for diagnosis in circumstances where the user is able to provide the report, since users will have access to this functionality. * Some features dependent on SKU

Top Issue Review #3 Fix email connection problems Common causes of email connection problems DNS records for your organization aren’t set up. DNS records for your organization need to be changed. Outlook profiles are set up to use a specific server name instead of using Autodiscover. Unsupported version of Outlook. #3 Fix email connection problems Common causes of email connection problems DNS records for your organization aren’t set up. An MX record is required to receive email. A CNAME Autodiscover record is required to allow connections through Outlook. An SPF record lets other organizations know your email came from a trusted source. DNS records for your organization need to be changed. If your organization was recently migrated or received a service update, you may need to update your DNS records. Outlook profiles are set up to use a specific server name instead of using Autodiscover. We need to be able to move mailboxes around for datacenter maintenance and service updates, so use of Autodiscover is required by your organization to make sure we don’t break things for you. Unsupported version of Outlook. The version of Outlook that you are using has to meet Office 365 requirements and should also have all of the latest updates applied. We recommend using Windows Update so that your version of Outlook always has the latest software updates. http://community.office365.com/en-us/wikis/solutions/fix-email-connection-problems.aspx

Troubleshooting domains Scenario Troubleshooting steps Problems with domain verification   Make sure TXT or MX record is entered correctly. Wait up to 72 hours for replication of TXT or MX record update. For a list of online tools that help with troubleshooting DNS propagation, click http://www.bing.com/search?q=dns+propagation+check. Use tools such as nslookup or network-tools.com to verify entries. Unable to verify domain Check whether the domain already exists in Office 365. Check whether part of the domain may be blacklisted. Unable to remove domain Make sure that MSO ID does not use the domain. Make sure that the email addresses do not use the domain. Make sure that the sub-domains of the domain do not exist. Problems with DNS settings, for example, MX, email Autodiscover, or Lync Autodiscover. Wait up to 72 hours. Use tools such as nslookup or network-tools.com to verify entries are added correctly.

Required DNS records Service Required DNS records Purpose Exchange Online MX record Configures email routing. CNAME record Autodiscover record that is used to help users easily set up a connection between Exchange Online and the user's Outlook desktop client or a mobile email client. TXT/SPF record Specifies that outlook.com, the domain that is used by the Office 365 mail servers, is authorized to send mail on behalf of your domain. Create this SPF record to help prevent your outgoing mail from being flagged as spam. Lync Online SRV record Helps enable federation with other instant messaging services, such as Windows Live or Yahoo! Autodiscover record that is used to help users easily set up a connection between the Lync desktop client and Microsoft Lync Online. Autodiscover record that is used to help users easily set up a connection between the Lync mobile client and Lync Online. SharePoint Online A record Routes traffic to your public-facing SharePoint Online website.

Top Issue Review #4 Delete or Restore User Mailboxes Common causes of email connection problems DNS records for your organization aren’t set up. An MX record is required to receive email. A CNAME Autodiscover record is required to allow connections through Outlook. An SPF record lets other organizations know your email came from a trusted source. DNS records for your organization need to be changed. If your organization was recently migrated or received a service update, you may need to update your DNS records. Outlook profiles are set up to use a specific server name instead of using Autodiscover. We need to be able to move mailboxes around for datacenter maintenance and service updates, so use of Autodiscover is required by your organization to make sure we don’t break things for you. Unsupported version of Outlook. The version of Outlook that you are using has to meet Office 365 requirements and should also have all of the latest updates applied. We recommend using Windows Update so that your version of Outlook always has the latest software updates. http://community.office365.com/en-us/wikis/solutions/fix-email-connection-problems.aspx

Delete or Restore User Mailboxes Can be deleted by: Deleting the user account Removing the Exchange Online License from a user Running the Remove-Mailbox cmdlet in PowerShell Exchange Online Retains the contents for 30 days, after this time the mailbox is permanently deleted and NOT recoverable Mailboxes can be recovered (no data lost) within the 30 day retention period Using Office 365 admin center (Deleted users section) Or reattaching license if license was removed http://technet.microsoft.com/en-us/library/dn186233(v=exchg.150).aspx You can delete Exchange Online mailboxes by deleting the corresponding Office 365 user account, removing the Exchange Online license, or by running the Remove-Mailbox cmdlet in the Shell. You can't use the EAC to delete a mailbox. When a mailbox is deleted, Exchange Online retains its contents for 30 days, by default. After 30 days, the mailbox is permanently deleted and is not recoverable. You can recover a deleted mailbox within the retention period by using the Office 365 admin center to recover the corresponding Office 365 user account. If the mailbox was deleted by removing the Exchange Online license, it can be restored within the retention period by reassigning the license to the corresponding user account. A recovered mailbox contains all the data stored in it at the time it was deleted. If you need to delete a mailbox, but preserve the mailbox contents indefinitely, you can enable an inactive mailbox. To do this, you have place the mailbox on In-Place Hold before you delete it. For more information, see Manage Inactive Mailboxes in Exchange Online. Note: Before an inactive mailbox can be enabled, the mailbox must be assigned an Exchange Online (Plan 2) license or have an Exchange Online Archiving subscription so that an In-Place Hold can be placed on the mailbox before it's deleted.

Top Issue Review #5 Troubleshooting Size limit Issues Exchange Online enforces message and recipient limits for sending and receiving messages SharePoint Online Storage and Other Limits No charge for storage until the need for more than the current licenses provide #5 Troubleshooting Size limit Issues Common causes of email connection problems DNS records for your organization aren’t set up. An MX record is required to receive email. A CNAME Autodiscover record is required to allow connections through Outlook. An SPF record lets other organizations know your email came from a trusted source. DNS records for your organization need to be changed. If your organization was recently migrated or received a service update, you may need to update your DNS records. Outlook profiles are set up to use a specific server name instead of using Autodiscover. We need to be able to move mailboxes around for datacenter maintenance and service updates, so use of Autodiscover is required by your organization to make sure we don’t break things for you. Unsupported version of Outlook. The version of Outlook that you are using has to meet Office 365 requirements and should also have all of the latest updates applied. We recommend using Windows Update so that your version of Outlook always has the latest software updates. http://community.office365.com/en-us/wikis/solutions/fix-email-connection-problems.aspx

Items removed from Deleted items Message Limits Size Limits Limit Value Message size limit 25 MB File attachments limit 125 attachments Subject length limit 255 characters Recipient limit (in single email) 500 recipients Message Rate Limit 30 messages per minute Recipient Rate limit 10,000 recipients per 24 hours Forward Limit (applies to rules) 10 recipients. Nothing forwarded if exceeded. Retention Limits http://technet.microsoft.com/en-us/library/jj907303(v=exchg.150).aspx Deleted Items Items removed from Deleted items Junk Email folder 30 days 14 days The limits applied to an Office 365 tenant may differ depending on how long the domain has been enrolled in the service. When a limit is changed in the Microsoft datacenters, it can take some time to apply the change to all existing tenants. You can't modify most of these limits, but you and your users should be aware of them. These limits apply to both internal and external recipients. 

SharePoint Online Storage Limits SharePoint Online – Storage & Other Limits Tenant Storage Quota Limit Increase – up to 25 (TB) Terabytes One Public-Facing Site per tenancy – 5Gb Site Collections – 300 Team Site Collections UP to 100GB (Gigabytes) Per Site Collection The Service Description contains a list of supported vs. unsupported features. http://go.microsoft.com/fwlink/?LinkId=207232 For SharePoint one additional key consideration is around the maximum storage allocation a tenant/company can have.   That ceiling is 25TB (Terabytes).  A key item to note is the My Sites allocation of 500MB per user, which does not count towards the 25TB storage pool limit.    Customers do not pay for storage until they need more than their licenses provide.  To calculate how much storage is actually allocated to a customer on initial provisioning, and to determine at what point a customer will have to purchase additional storage, the following equation should be used:  10GB+(500MB*E1/A1-E4/A4 seats purchased).  For a 10,000 seat customer, they would get 5TB of pooled storage upon initial provisioning.  If they need more for team sites, etc., they could buy up to 20TB more of storage at $.0.20/GB/Month (which puts them at the cap of 25TB). ** NOTE ** The 500 MB listed in the calculation is not the MySites 500MB per user allocation.  During initial provisioning, an E user contributes 500MB of storage to the company’s storage pool. The plan is for the A1-A4 plans/skus to mirror the E1-E4 plans/skus except for the EDU specific features. There will be some of the larger Edu and Enterprise customers who “get” more than they can physically have, across both team sites and personal sites.  Here are some new resources to get up to speed on what’s new, pointers to both internal and external information: External (please share these resources broadly): SU2 all up blog post on The SharePoint Team Blog: http://sharepoint.microsoft.com/blog/Pages/BlogPost.aspx?pID=1004 Deeper dive into the PDF management improvement: http://sharepoint.microsoft.com/blog/Pages/BlogPost.aspx?pID=1005 Our Storage update (25TB and 92% reduction in price): http://sharepoint.microsoft.com/blog/Pages/BlogPost.aspx?pID=1010 DO NOT SHARE OUTSIDE OF MICROSOFT FTEs Internal (MS FTE only): Updated SPO XL Scale limits BOS Wiki article (Q2 CY 2012 Briefing, post-SU2 roll out): https://spsites.microsoft.com/sites/bosm/boswiki/Pages/SharePoint-Online-Scale-Limitations--Q2-CY-2012-briefing-statement.aspx ** A key item to note is the My Sites allocation of 500MB per user, which does not count towards the 25TB storage pool limit. **OneDrive has a 1GB storage per user – Unmanaged

Troubleshooting OneDrive Issue Details Credentials required Some circumstances may require you to re-enter your log-in credentials for a library you’re syncing on your computer. When a library requires your credentials, an exclamation point icon overlays the OneDrive for Business icon in your system tray We can’t sync this library because it’s too large OneDrive for Business can sync up to 20,000 items in the OneDrive for Business library, including folders and files. For other libraries, such as libraries on team sites, OneDrive for Business can sync up to 5000 items, including folders and files. This library isn’t available offline Options set for this library by your administrator prohibit users from syncing it to a local computer. For more information, see your SharePoint administrator. This site isn’t available offline This library is hosted on a SharePoint site that prohibits syncing libraries to a local computer. For more information, see your SharePoint administrator. Credentials required Some circumstances may require you to re-enter your log-in credentials for a library you’re syncing on your computer. When a library requires your credentials, an exclamation point icon overlays the OneDrive for Business icon in your system tray: To see details about the problem, click the OneDrive for Business icon, and then click View sync problems to open the “We ran into problems syncing” error dialog box. To fix this problem, close the error dialog box, open a web browser, and sign in to SharePoint Online. This should restore normal synchronization for the library. We can’t sync this library because it’s too large OneDrive for Business can sync up to 20,000 items in the OneDrive for Business library, including folders and files. For other libraries, such as libraries on team sites, OneDrive for Business can sync up to 5000 items, including folders and files. This library isn’t available offline Options set for this library by your administrator prohibit users from syncing it to a local computer. For more information, see your SharePoint administrator. This site isn’t available offline This library is hosted on a SharePoint site that prohibits syncing libraries to a local computer. For more information, see your SharePoint administrator.

Resources O365 Community O365 Product Blog Office Configuration Analyzer Tool (OffCAT)

O365 Community Deliver a vibrant community experience that enables our customers and partners to efficiently find information, and receive best-in-class support. Logged in Customers can post questions, Anonymous users can view questions Forums Forums O365 Community Self help tool to help customers walk through issues and identify solution assets DIY - Troubleshooter DIY Wiki Knowledge based articles on specific support topics Wikis Blogs Searching within the Community displays ranked and rated help content from various MS properties including: Office.com & O365 Community in an easily consumable format *Search Community Manager blogs on timely and relevant topics Blogs http://community.office365.com/en-us/default.aspx

Office 365 team blog Latest news, tips and videos from the Office 365 team at Microsoft Useful information and case studies which can be used for internal and customer purposes http://blogs.office.com/b/microsoft_office_365_blo g/

Office Configuration Analyzer Tool (OffCAT) Provides a detailed report of installed Office programs Report includes many parameters about Office program configuration Highlights known problems found when OffCAT scans the PC Problems that are listed in the report, provide a link to a public- facing article (usually a Microsoft KB article) on the issue Report can be saved to a file so that the report can be viewed in the Office Configuration Analyzer Tool on another PC where the tool is installed http://support.microsoft.com/kb/2812744 http://aka.ms/offcat

Office 365 Product Pages Useful FAQ and product information Not specific, but a good place to get high- level information on the different plans etc. www.microsoft.com/office365

TechNet De facto source for technical product information Should be one of the first resources you refer to for technical product information Service descriptions the “bible” of Office 365 http://aka.ms/o365technet