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The art of
troubleshooting
Office 365
Kristina Ashment
Program Manager
Mail Flow Topology
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.
Common 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.
Troubleshooting
Mail flow
Message trace
Delivery Reports
Guided Walk through
Inline Request Support
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 Example
6/21/2013 3:18:54 AM
FAIL
The message was not delivered.
Delivery Reports
Email sent to another mail system
Sent but no MX Record for destination*
Delivery Report for [email protected]
([email protected])
All Exchange can report is that the
message is out side of its reporting
Submitted
boundary since it is now the processing
19/06/2013 10:23 AM
responsibility of the other mail system.
The message was submitted.
NDRs, if any, will have to be returned by
the other mail system.
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.
Delivery Report for [email protected]
([email protected])
Submitted
19/06/2013 10:29 AM
The message was submitted.
Message stays in
pipeline and retries for
48 hours
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 – two hours later
Email sent internally and verified received
Delivery Report for Amy
Alberts ([email protected])
Submitted
19/06/2013 10:33 AM
The message was submitted.
Since the recipient is internally handled
by the same mail system. Delivery can
be confirmed.
Delivered
19/06/2013 10:33 AM
The message was successfully delivered.
Service acknowledges
Pending
delay
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 days later
Failed
6/21/2013 10:32 AM
The message couldn't be delivered.
An NDR will be returned
by the internal Exchange
service at this stage.
* This scenario applies in many circumstances where the destination
mail server is unresponsive.
Message Trace & Delivery Reports
Message Trace
Delivery Report
Accessed by
Administrators only
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
* Some features dependent on SKU
Troubleshooting domains
Scenario
Troubleshooting steps
Problems with domain verification
1.
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.
2. Use tools such as nslookup or network-tools.com to verify entries.
Unable to verify domain
1.
Check whether the domain already exists in Office 365.
2. Check whether part of the domain may be blacklisted.
Unable to remove domain
1.
Make sure that MSO ID does not use the domain.
2. Make sure that the email addresses do not use the domain.
3. Make sure that the sub-domains of the domain do not exist.
Problems with DNS settings, for
example, MX, email Autodiscover, or
Lync Autodiscover.
1.
Wait up to 72 hours.
2. Use tools such as nslookup or network-tools.com to verify entries are added
correctly.
Required DNS records
Service
Purpose
Exchange Online
Exchange Online
Required DNS
records
MX record
CNAME record
Exchange Online
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!
Lync Online
CNAME record
Autodiscover record that is used to help users easily set up a connection between the
Lync desktop client and Microsoft Lync Online.
Lync Online
CNAME record
SharePoint Online
SharePoint Online
A record
CNAME record
Autodiscover record that is used to help users easily set up a connection between the
Lync mobile client and Lync Online.
Routes traffic to your public-facing SharePoint Online website.
Routes traffic to your public-facing SharePoint Online website.
Configures email routing.
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.
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
Use In-Place hold to delete mailbox but retain contents.
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
Deleted Items
Items removed
from Deleted items
Junk Email folder
30 days
14 days
30 days

•
•
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.
The slowest 1% of pages
in SharePoint online take
more than 5,000ms to
load
1,000ms
5,000ms
Why SharePoint pages get slow…
CDN
Server
Browser
Network
Server
Network
Microsoft
Network
ISP
Internet
Complex pages
Too many web parts
Expensive server interactions
Front end cache misses
Large payload
Too many files
Large distance to server
Complex pages
Busy computer
Small cache
Top 5 causes of slow performance
Front end caches in SPO
SharePoint On-premises
10s of servers
10s of busy sites
100s of users
SharePoint Online
1,000s of servers
1,000s of busy sites
10,000s of users
Perf tips: Structural Navigation
•
•
•
Fewer sites, less work
Will reduce server time but still have slower requests in higher percentiles (cache
misses)
•
•
Uses managed metadata – much faster than iterating over all sites
No security trimming in navigation
•
•
Uses a search query to get site structure
Can cache navigation in client storage
•
•
Perf tips: Content rollup
•
•
•
Less scope, less work
Will reduce server time but still have slower requests in higher percentiles (cache
misses)
•
•
•
New in SPO!
Uses search queries to get results
Very rich functionality with search customization
•
For content that seldom changes, use static content
Common links, department sites, etc.
•
•
•
Perf tips: Image optimization
•
•
•
Compress images before uploading them to SharePoint
Use renditions
•
•
Very valuable in high-latency scenarios
Focus on first loading “above the fold” content before content deeper in the page
•
Perf tips: Optimize HTTP traffic
•
•
•
•
Deliver static content via CDN’s if possible
Parallelize downloads across multiple hostnames
Bundle static assets together to reduce HTTP requests
•
•
Minify all JavaScript and CSS assets
Use image sprites for common static images
•
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
OneDrive for Business can sync up to 20,000 items in the OneDrive for
We can’t sync this library Business library, including folders and files. For other libraries, such as libraries
because it’s too large
on team sites, OneDrive for Business can sync up to 5000 items, including
folders and files.
This library isn’t available Options set for this library by your administrator prohibit users from syncing it
offline
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.
Demo
Guided Walkthrough
OneDrive for Business – Initial Sync Setup Guide
http://aka.ms/odbsyncsetup
OneDrive for Business Sync App (formerly SkyDrive
Pro) – Sync Issues Guide
http://aka.ms/odbsyncissues
Additional
Troubleshooting
Tools
Office Admin Center - Tools
DIY Troubleshooter
Remote Connectivity Analyzer
Office Configuration Analyzer
http://aka.ms/offcat
Complete list of tools by SKU
Guided Walkthroughs by Area:
Complete list located
http://support.microsoft.com/kb/
2934107
Office Configuration Analyzer Tool (OffCAT)
http://aka.ms/offcat
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.
Forums
DIY - Troubleshooter
O365
DIY
Community
Self help tool to help
customers walk
through issues and
identify solution
assets
Forums
Logged in Customers
can post questions,
Anonymous users can
view questions
Wiki
Wikis
Knowledge based
articles on specific
support topics
Blogs
*Search
Blogs
http://community.office365.com/en-us/default.aspx
Community Manager
blogs on timely and
relevant topics
Searching within the Community
displays ranked and rated help
content from various MS
properties including: Office.com &
O365 Community in an easily
consumable format
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 365 Product
Pages
Useful FAQ and product information
Not specific, but a good place to get highlevel 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
Thank you
Appendix
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 Info Example




Diagnostic information for administrators:
Generating server: contoso.com
[email protected]
cdptpa-contoso.mail.com #550 5.1.1 - Invalid
mailbox: [email protected] ##
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.
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 autocomplete 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.