OFFICE 365 Outlook Troubleshooting Steps

Table of Contents

1: CHECK IF MAILBOX IS MIGRATED TO OFFICE 365 .................................................................. 2

2: CHECK IF USER LOGGED ON TO PC WITH AD ID ................................................................... 2
3: CHECK THE CONNECTION VIA TELNET ................................................................................ 3
4: CHECK IE PROXY SETTINGS ............................................................................................. 4
5: CHECK THE OUTLOOK COMPATIBILITY ............................................................................... 4
6: CHECK THE CONNECTION .............................................................................................. 5
7: SET PROXY SERVER FOR BYPASSING .................................................................................. 6
8: SET PROXY SERVER WITHOUT SELECTING BYPASS OPTION ....................................................... 8
9: OUTLOOK REPAIR IN CASE OF OUTLOOK FAILURE OR CORRUPTION. ............................................ 8
10: OPEN OUTLOOK IN SAFE MODE TO DISABLE ALL THE ADD-INS AVAILABLE .................................... 9
11: OFFICE 365 MAILBOX MANUAL CONFIGURATION STEPS ..................................................... 10
12: CHECK THE OUTLOOK CONNECTIVITY VIA “MICROSOFT REMOTE CONNECTIVITY ANALYZER” .......... 17
13: SERVER OPERATION ESCALATION, IF ABOVE STEPS DIDN ’T WORK ……………………………………..……20
14: SERVER OPS, IF INTERNET IS NOT ACCESSIBLE WITH “AUTOMATICALLY DETECT SETTINGS”……………21
15: UPDATE THE RESULTS IN TRACKER ……..………………………………………………….……………………….23
16: IF OUTLOOK REPEATEDLY ASKS FOR PASSWORD DURING CONFIGURATION………………………………..24

Version No: 1.1

Created By: L2 Team
Reviewed By: Sreenivas Murthy
Approved By: Sreenivas Murthy
Step 1: Check if mailbox is migrated to Office 365
1.1 Login to webmail from browser with URL https://webmail.wipro.com
1.2 Enter User name and password
1.3 If the page is prompting to use Office 365 URL, then user mailbox is in
cloud.

Step 2: Check if user logged on to PC with AD ID

2.1 Open command prompt ( Start  Run cmd)
 2.2 Type “whoami” and compare with the user AD ID

Step 3: Check the connection via Telnet

3.1 Install telnet (start  run cmd)
3.2 Type pkgmgr /iu:"TelnetClient"

3.3 Type telnet outlook.office365.com 443

3.4 Check if able to telnet or not

3.5 If unable to telnet, ensure the details are captured in the excel
Step 4: Check IE proxy settings
4.1 Open Internet Explorer and go to LAN settings (Internet options 
Connections  LAN Settings)

4.2 Set to Automatic Configuration by selecting the option Automatically

detect settings

4.3 Open the OWA using the URL https://outlook.com/owa/wipro.com

Step 5: Check the Outlook compatibility

5.1Below are the compatible Outlook versions of Office 365
5.1.1 Outlook 2007 SP3 with patches until December 2012 will make
the Outlook.exe to 12.0.6665.5000 or later version

The 2007 Microsoft Office Suite Service Pack 3 (SP3) -http://www.microsoft.com/en-

us/download/details.aspx?id=27838

Update - Outlook 2007 update 2863811 - http://www.microsoft.com/en-

us/download/details.aspx?id=42427

5.1.2 Outlook 2010 with SP2 will make the Outlook.exe to

14.0.7015.1000 or later version.

2010 SP2 - http://www.microsoft.com/en-us/download/details.aspx?id=39667

Outlook update (Outlook 2010 hotfix package April 8, 2014) -

http://support.microsoft.com/kb/2878254
 5.1.3 Outlook 2013 will make the Outlook.exe to 15.0.4420.1017 or
later version

5.2 Outlook.exe can be found in C:\Program Files\Microsoft

Office\OfficeXX\Outlook.exe

Step 6: Check the Connection

6.1 Restart or Launch the Outlook
6.2 Start  Run cmd
6.3 Type tasklist | findstr /i outlook

6.4 Note the PID (eg: 1300)

6.5 Type netstat –ano –t 2 | findstr /I PID

Note: Copy/paste of cmdlet will not work; do type in the cmdlet in command prompt
 6.6 Note the below details to conclude that connection is routing through
firewall.
6.6.1 The IP address will be from the range attached below. (URL:
http://technet.microsoft.com/en-us/library/hh373144.aspx)

EXchange Online IP
Addresses.xlsx

6.6.2 The Outlook will always rout via the port number 443.
6.6.3 The connection Status should be ESTABLISHED
6.6.4 Also note the PID (e.g.: 1300)

If above steps are not resolving the issue go to Step 7

Step 7: Set Proxy server for bypassing

7.1 Open Internet Explorer and go to LAN settings (Internet options 
Connections  LAN Settings)
7.2 Select the option Use a proxy server for your LAN and set the location
proxy
7.3 Open Internet Explorer and go to LAN settings (Internet options 
Connections  LAN Settings)
7.4 Select the option Use a proxy server for your LAN and set the location
proxy
7.5 Click on Advanced

7.6 Add the below addresses as exceptions along with the existing entries
outlook.office365.com;autodiscover.service.wipro.com;wipfs01.wipro.com
If step 7fails go toStep 8

Step 8: Set Proxy server without selecting Bypass option

8.1 Open Internet Explorer and go to LAN settings (Internet options 
Connections  LAN Settings)
8.2 Select the option Use a proxy server for your LAN and set the location
proxy
8.3 Make sure that Bypass proxy server for local address is unchecked.

Step 9: Outlook Repair in case of outlook failure or corruption.

9.1 Click Start > Control Panel > Programs > Programs and Features.
9.2 Click the Office program you want to repair, and then click Change.
9.3 Do one of the following:
9.1.1 In Office 2010, click Change > Repair -> Continue
Step 10: Open outlook in safe mode to disable all the add-ins available

Note: If the outlook is crashing, try open outlook in safe mode to avoid loading
unwanted add-ins available on the desktop/laptop.

10.1 Close the existing outlook application and make sure its not available
in running process.

10.2 Go to Run-> and type in Outlook / Safe

 10.3 You must be able to login to outlook now.

Step 11: Office 365 Mailbox Manual configuration steps

1. Open control panel and follow the below steps to create a profile
2. Click on Mail  Add

3. Enter Profile name

4. Change the selection to ‘manually configure server..’
5. Select “Microsoft exchange or ….”

6. Provide the server name as below

Server: pod51054.outlook.com or outlook.office365.com

User name: AD ID for the user

 Note: Make sure cached exchange mode is enabled

7. Click on “More Settings” and select the “connection” tab

8. Click on “connect to Microsoft Exchange using HTTP” box

Key in below details as per screenshot

pod51054.outlook.com or outlook.office365.com

msstd:outlook.com
9. It will prompt for user name and password, Type in the password in below
format

10. It must resolve with the below wizard.

 11.Click on Next to finish the setup.

NOTE: Microsoft doesn't support manually setting up a profile in Outlook for connectivity to
mailboxes in Exchange Online in Office 365.

Step 12: Check the outlook connectivity via “Microsoft Remote Connectivity
Analyzer”
12.1 Open Internet Explorer and type in below url

https://testconnectivity.microsoft.com/

12.1 Select “Office365” tab and click on “Outlook Connectivity” as per below
screenshot
12.3 Click on ‘next’ in below of the page

12.4 Fill the entire required field using affected user’s credentials,
 12.4 Please wait until the Analyze to complete

12.5 You must receive the below successful connectivity test result, the
below test result shows the connectivity from your system is capable of establishing
outlook connectivity.
 12.6 In case of failure result, export the result in XML format and share with
Server Admin team for further investigation.

Step 13: Server Operation Escalation, if above steps didn’t work

Note: If the entire above test request appears positive and still unable to configure,
you can get in touch with Server Operation team to know the below values are set
correct from the Office365 mailbox side.

13.1 Make sure the below Attributes are in place in AD

Attribute Example

Mail ted@wipro.com

mailNickname Ted

displayName Ted Bremer

proxyAddresses SMTP: ted@wipro.com X400:c=us;a= ;p=First Organization;o=Exchange;s=Bremer;g=Ted

13.2 Make sure the secondary smtp address “*service.wipro.com” is

stamped properly.

13.3 Check the user is been assigned with appropriate license.

Note: Kiosk license users cannot connect to outlook client.

13.4 Check the MAPI is set as true by using below PowerShell cmdlet

Get-CASMailbox –Identity “Alias” | fl *MAPIEnabled*

Step 14: Server Operation Escalation, if you are not able to access internet
with “Automatically detect settings”

Note: Steps to be checked by Server Team

1. Go to DHCP Server Options and check option 252(Auto Proxy) is enabled for the Server

2. Validate the Auto Proxy string for respective location

Location wise Proxy string

BDC/ROB - Proxy 1 http://10.201.51.71/accelerated_pac_base.pac

http://Proxy1.wipro.com/accelerated_pac_base.pac
BDC/ROB - Proxy 4 http://10.201.51.54/accelerated_pac_base.pac
http://Proxy4.wipro.com/accelerated_pac_base.pac
PDC - PDC Proxy http://10.113.50.55/accelerated_pac_base.pac
http://PDC-Proxy.wipro.com/accelerated_pac_base.pac
HDC - HDC Proxy http://10.156.50.99/accelerated_pac_base.pac
http://HDC-Proxy.wipro.com/accelerated_pac_base.pac
GNDC - GNDC Proxy http://10.107.4.44/accelerated_pac_base.pac
http://GNDC-Proxy.wipro.com/accelerated_pac_base.pac
KDC - KDC Proxy http://10.141.1.25/accelerated_pac_base.pac
http://KDC-Proxy.wipro.com/accelerated_pac_base.pac
SJP - SJP Proxy http://10.101.50.71/accelerated_pac_base.pac
http://SJP2Proxy.wipro.com/accelerated_pac_base.pac
Cochin - Cochin Proxy http://10.222.50.22/accelerated_pac_base.pac
CDC - [CDC] Proxy 2 http://10.145.22.10/accelerated_pac_base.pac OR
CDC http://Proxy2.wipro.com/accelerated_pac_base.pac
US http://SCProxy.wipro.com/accelerated_pac_base.pac
Melbourne http://mel-proxy.wipro.com/accelerated_pac_base.pac
Adelaide http://10.110.9.15/accelerated_pac_base.pac
Dubai http://du-proxy.wipro.com/accelerated_pac_base.pac
Chengdu http://chengdu-proxy.wipro.com/accelerated_pac_base.pac
Saudi http://10.100.92.240/accelerated_pac_base.pac
UK http://rdc-proxy.wipro.com/accelerated_pac_base.pac
Japan http://samurai.wipro.com/accelerated_pac_base.pac
shanghai http://dragon.wipro.com/accelerated_pac_base.pac
Sydney http://10.110.1.10/accelerated_pac_base.pac
Malaysia http://kl-proxy.wipro.com/accelerated_pac_base.pac
Singapore http://wt-sgn-proxy.wipro.com/accelerated_pac_base.pac
Sydney Sales http://syd-sales-proxy.wipro.com/accelerated_pac_base.pac

3. Go to each Scope Options and Check whether Auto Proxy is enabled for the particular scope

4. Disable the Auto Proxy scope option by unchecking option 252 in respective scope options

5. Apply and OK
 6. Check whether the scope is taking option 252(Auto Proxy) from server Options

Step 15: Update the results in tracker as per the below format and send the
daily report to Office365 Program office365.program@wipro.com
IP Ticket
Location Address No Issues Action Taken Status Next Action
Traffic not passing
Backbone through automatic Made the manual working / TO be updated to
/ EC 1.1.1.1 12345 settings settings for the proxy Open Network team
16: If Outlook repeatedly asks for password during configuration, follow
below steps.

Kindly enter the full name of the user in the username field like below and then check name &
also try with the below registry settings.

 StartRunRegeditgo to the below path

 Right click on outlook folderNewKeyType the key name RPC

 Right click on RPC folder NewDWORD Value ( If the OS is 64bit select QWORD
value)  Type the Key name Usewindowsusercredentials

 Make sure the Value is “0”