Author Archives: admin

Exchange Server 2019 is a single server role architecture and it is easy to deploy. I have share the details on how to install Exchange Server 2019 in my blog and here we will see the post installation steps to make the Exchange Server 2019 fully functional.

I’m just sharing basic information post installation steps that you need to do after Exchange Server 2019 installation.

Step 1: Create a Send connector to send emails to External Domain.

By default, there is no option to send an email to external domain. We have a manually create a send connector to send emails to external domain.

Step 2: Create Accepted Domains

Domain in which Exchange 2019 installed will be authoritative by default (domain.local) etc and if we want to have an email address like, we need to create an accepted domain with the name

Step 3: Configure Email Address Policy

We have created Accepted domain in the above steps and to stamp that email address to the recipients, we need to configure the default email address policy and apply the email address policy to all the mailboxes

Step 4: Configure Exchange Certificate

All the services in use to be configured to use SSL instead of self-signed certificate and certificate to be configured for all the services

Step 5: Configure Exchange Virtual Directory External and Internal Urls and Authentication Methods

Services that are published external to be configured with the external Url and internal urls to be modified as per the design plan. Ensure you have configured the right Authentication Method for each Virtual Directory

Step 6: Configure Load Balancing for Client Access Urls

Once the Virtual directory settings are configured, we can consider to configure load balancing for all the Client Access Protocols

Step 7: Verify all types of client connections to Exchange

Check the Outlook connectivity, Auto Discover, OWA, ECP, EWS, Exchange Active Sync, Outlook Anywhere client connection.

Step 8: Setup Monitoring and Alerting

One of the must have thing for Exchange environment is to have proper monitoring solution to monitor and alert if any issues in Exchange.

Step 9: Setup Mobile Device configuration

We can consider to have Mobile Device Access Policies based on the company security standards if Users are allowed to access their mailbox using Mobile devices.

Step 10: Secure Mail Flow

Ensure you have proper Anti-Spam and Anti Malware scanning available for mail flow by configuring the default malware scanning engine or route inbound and outbound mail flow via Exchange Online Protection.

Leave your comments for any queries on the above.

If your mailbox hosted in Office 365 and experiencing slowness while accessing the mailbox using outlook, you need to check below things before raising a ticket with Microsoft.

  • Check the Global DNS Resolution

It is always better to check whether your connection goes the closest regional office 365 datacentre. If your Office 365 tenant hosted in US and you are accessing your mailbox in US but the DNS resolution to Singapore ingress point, then you may to need to contact your ISP to identify/fix the issue.

Check the host name resolution for Below connecting to as I’m in sitting in India.






NSLOOKUP will show the nearby Ingress endpoint name. Below the ingress point available at office 365 and the location details

  • Check the network latency using ping or psping test

If you are experiencing slowness in accessing your Office 365 Mailbox, you can check the network latency to using ping test, average latency should not exceed 300 ms.

  • Outlook Connection Status

Check the Outlook Connection Status by focussing the Average Request and Average Response. You can calculate the round trip time using RTT = Average Request – Average Response which has to be less than 300 ms

  • Trace Route to find the number of hops to reach Microsoft network

Use the tracert command to to check the number of hops it is taking to reach the Microsoft network (

  • TCP Idle session

TCP time out has to be configured more than 2 hours on the perimeter devices like firewall and other network devices

  • check the latency when using Proxy and a direct internet connection

Most of the organization use proxy server to allow the clients to connect to internet. Check the latency when using proxy and without proxy and if proxy shows more latency check if you can bypass it

  • Disable the outlook Add-Ins to see if any Add-Ins is causing a Problem.

Outlook -> File -> Options -> AddIns -> Manage Add-Ins

  • Also you can use SARA Tool to find any issues in Outlook issues

Above are the basic things that we can check to see if any issue at the end user side. If everything looks normal, then raise a ticket with Microsoft 😉

How Azure AD Connect Works

December 24th, 2018 | Posted by admin in Azure AD - (0 Comments)

Azure AD Connect is the upgraded version of DirSync which is used to provision the On-Premise Objects into Azure Active Directory. There are many ways that can be used to provision the Objects to Azure AD for Office 365 like,

  • Directory Synchronization (DirSync), Office 365 Portal, Windows PowerShell, or API
  • Microsoft Azure AD Connector for FIM 2010 R2
  • Microsoft Azure Active Directory Sync tool (Azure AD Sync Tool)
  • The New Microsoft Azure AD Connect

We will see how the Azure AD Connect works on this post. Directory Sync or the Azure AD Connect is mainly required for Identity Federation and Exchange Hybrid Deployment. Below the flow diagram of how the Azure AD Connect works

Azure Connect support the below features

How Azure AD Connect works?

Azure AD Connect by default is a one-way Sync which synchronize the On-Premise AD objects to Azure AD. Before looking at the Synchronization Data Flow, we will see what are Management Agents and where AD Connect stores the information

Management Agents

Management Agents in Azure AD Connect control the data flow between a connected data source and the meta directory. DirSync or Azure AD Connect uses two managements agents.

  • Active Directory Connector management agent
  • Microsoft Azure Active Directory management agent

DirSync or Azure AD Connect stores the information in two places:

  1. Connector Space

Connect Space has the Replica of the managed objects in the AD DS and each management agent or connector has its own connector space

  1. Metaverse

Aggregate information about a managed object (that is, User, Group, etc.)

Azure AD Connect Synchronization data flow:

  1. User is imported from On-Premise AD into the Active Directory Connector space
  2. User is projected to the Metaverse
  3. User is provisioned to the Microsoft Azure Active Directory Connector space
  4. User is exported to the Office 365 Admin Web Service

Above explains how the Azure AD Connect synchronize the objects from On-Premise AD to Azure AD. If Exchange Hybrid option is selected which installing/configuring the Azure AD Connect, then below 7 attributed will be written back to On-Premise AD. (Exchange Federation is must for below Objects to write back to On-Premise AD).


Online Archive: Enables customers to archive mail.


Enable Unified Messaging (UM) – Online voice mail: This new attribute is used only for UM-Microsoft Lync Server 2010 integration to indicate to Lync Server 2010 on-premises that the user has voice mail in online services.


Litigation Hold: Enables cloud services to determine which users are under Litigation Hold.

(LegacyExchangeDN as X500)

Enable Mailbox: Offboards an online mailbox back to on-premises Exchange.


Filtering: Writes back on-premises filtering and online safe and blocked sender data from clients.


Forward Sync and Back Sync in Azure AD Connect

It is important to know what is forward sync and back sync in Azure AD Connect.

Forward Sync

It is sync from Azure AD to the Online Application directory services

  • Once the AD Objects from On-Premise synced to Azure AD, Azure AD won’t be directly referred by office 365 online application.
  • Each online application in Office 365 has their own directory service. After an object is changed in Azure AD, further synchronization are constantly running that parse relevant changes and ship them to these services’ directory partitions.
  • Since the Application directory are updating the information from Azure AD, it can cause delay in applications becoming available to newly commissioned accounts or users

Back Sync or write Back

When Exchange Hybrid Configuration feature is enabled while configuring AD Connect, there are certain attributes for the Microsoft Exchange Online service that require reverse propagation to the on-premises environment for Exchange co-existence features to work which is referred as Back Sync.

  • Back-Sync: Data is changed in the Exchange Online partition and then synced back to Azure AD using daemons similar to those used for Forward-sync
  • Write-back: Data is shipped from Azure AD directory, back through Admin Web Service, to DirSync service using bi-directional FIM functionality
  • DirSync updates the local AD DS objects with these updated attributes

I hope this post is informative, please leave your comments if any additional information required.

On the last part, we saw how the auto discover works for customers in Office 365 alone. In this post we will see how the Autodiscover working on Exchange On-Premise and Hybrid Edge environment.

How Autodiscover works in Exchange On-Premise?

If a company has their messaging infrastructure in On-Premise alone, this is how the Autodiscover works for Exchange Online Mailbox

  1. Once the user launches the outlook and enter the credential, Outlook will query AD for SCP record to get the Autodiscover Service information.
  2. Once the information available, it will validate the user and try to connect the url which will go to the client access server
  3. CAS server query AD and send the Autodiscover and other exchange related services information in XML file
  4. Outlook uses that information to configure outlook profile.

Below the Test E-Mail Autoconfiguration result that explains the above behaviour

How Autodiscover works in Exchange Hybrid Environment?

Hybrid Exchange environment is nothing but a customer having few mailboxes in On-Premise Exchange and few in Office 365 (Exchange Online). Though both the exchange infrastructure are different, Hybrid Configuration Wizard make those 2 environments coupled together and function as a single environment.

Below the details on how Autodiscover works for a user mailbox in Office 365 for Hybrid environment user.

In above illustration, company user as their SMTP address space and for the mailboxes in Office 365, On-Premise will have a remote mailbox account with the target address as as the target address.

  1. Once the user launches the outlook and enter the credential, Outlook will query AD for SCP record to get the Autodiscover Service information.
  2. Once the information available, it will try to validate the user and it can’t find mailbox for Raj and only remote mailbox account available for this user in On-Premise and it will inform outlook to try Autodiscover request for Raj’s Target Address.
  3. Outlook will try to get the Autodiscover information for by dns query to internet. will have a CNAME record that points to Exchange Online Autodiscover record
  4. Outlook will connect which will connect to Exchange Online client Access server
  5. Exchange Online validate the user by an authentication prompt
  6. Once verified, Exchange Online will send the Autodiscover information in xml formal to user.

Below the Test E-Mail Autoconfiguration result that explains the above behaviour which clearly shows the above explanation

We see lot of information on how the Autodiscover works for Exchange Online, Exchange On-Premise and Hybrid Exchange environment with explanations. I hope this is informative to you. Leave your comments if any additional information required.

On the last part, we saw how the auto discover works for internal and external clients. In this post we will see how the Autodiscover working on Exchange Online.

How Autodiscover works in Exchange Online?

If a company has their messaging infrastructure in Office 365 alone without any On-Premise infrastructure, this is how the Autodiscover works for Exchange Online Mailbox

  1. When user enters the credential, it will perform a SCP query and it will fail
  2. DNS lookup will happen to find the Autodiscover service for the FQDN
  3. Once it finds the Autodiscover record, there will be CNAME record created for Autodiscover pointed to Here it is pointed to connect Exchange Online to get the Autodiscover information
  4. Outlook will connect (Exchange Online) and the credential will be validated.
  5. Autodiscover xml file will be returned to outlook client with the server name to connect as

Below test connection result show the details on how it worked. For testing, I have directly entered the email address, so the SCP query is not available on the below result.


Lot of tools are available to see the behaviour of Autodiscover like Outlook Test E-mail AutoConfiguration, Exchange Remote Connectivity Analyser, Fiddler and outlook advanced logging etc. Here we will use the Outlook Test E-mail AutoConfiguration option to explain the Autodiscover Process.

All the requests to Office 365 are considered as external network request and it behaves the same way as explained in the previous article.

  1. Second portion of the email address is considered as a the fqdn and it try to connect to that Url and it failed

  1. Outlook uses the predefined URL as mention below to connect and it failed again

  1. Searching for any local record for domain name and it failed

  1. Redirection method (HTTP instead of HTTPS to predefined URL) followed and it got response to go to It will prompt to enter the credential for validation at this point

  1. Got response for https & http of and for xml will retrieved from Exchange Online and outlook configures the profiles

This is how you need to split the log to see how the Autodiscover working on your environment.

Everyone knows how Exchange Autodiscover works, as it is there from Exchange Server 2007. Writing this blog to show how it works for Exchange Online, Exchange On-Premise and Exchange Hybrid environment.

Microsoft Exchange Autodiscover service in Exchange helps the Autodiscover capable outlook clients to configure outlook profile easily by providing minimal input. Users know their user name and password information, by providing those information, other information to configure outlook profile can be retried from Exchange using Autodiscover Service. Autodiscover automatically configures user profile for outlook and mobile devices.

Outlook 2007 and later clients supports Autodiscover to connect Exchange 2007 and above.

How Autodiscover works?

Information that are required to configure the outlook profile will be retrieved from Exchange in a XML format and outlook use that information to connect to different services to function properly.

How Autodiscover works when connecting from Internal network.

Note: To locate Autodiscover service, outlook uses LDAP query to Service Connection Point object first (Internal clients) and if it fails it uses DNS query (external clients).

  1. Once user enters the credential (email address and password, where email address is considered as a user name), outlook authenticated with AD and queries for Service Connection Point objects to find the Autodiscover Service in Client access server to which it has to contact to get the Autodiscover information in xml format.

SCP object will be created when Exchange client access server installed and new SCP will be created when new CAS servers are installed, SCP will be updated with the servicebindinginformation FQDN of client access server name in the form of and keyword that tells to which site this CAS server belongs.

Once the client authenticated to active directory,

  • The Autodiscover service information will be obtained from SCP object, for any reason it that fails
  • Outlook will try the predefined URL like by using DNS
  • If the above fails, outlook will try the HTTP redirect method, it is same predefined URL, instead of https, http will be used
  • If the above fails, SRV record lookup will be used which is the last lookup method and if that fails outlook auto configuration will fail.
  1. Autodiscover Service in CAS server contacts AD to get the URL and the configured Exchange Services details
  2. Autodiscover Service returns a HTTPS response with XML file that includes connection settings and URLS for available Exchange features
  3. Outlook client uses that information to connect to Exchange.

How Autodiscover works when connecting from Internet.

If the Client Machine is not domain joined, or connecting from Internet.

  1. Outlook first tries to locate the Autodiscover service by looking up the SCP object in Active Directory. Since the client is in internet, it will not be able to contact Active Directory,
  2. Outlook Client will try to locate the Autodiscover service by DNS query.

For DNS query, outlook uses the right side of the email address (domain name), that is,, and then check the DNS for two predefined URLs. For example

Note: Need to create a DNS record in Internet to connect to your Client Access Server to make it work.

  1. Autodiscover Service in CAS server contacts AD to get the URL and the configured Exchange Services details
  2. Autodiscover Service returns a HTTPS response with XML file that includes connection settings and URLS for available Exchange features
  3. Outlook client uses that information to connect to Exchange.

On the next part we will see how the Autodiscover work for Exchange Online / Exchange On-Premise and Exchange Hybrid environment.

When Outlook Clients connect to Autodiscover Service?

December 24th, 2018 | Posted by admin in Exchange - (0 Comments)


Outlook and Exchange Active Sync on mobile device uses Autodiscover for configuring and maintaining server settings for client that is configured to access a Mailbox. On the Initial configuration, we know Outlook will do an Auto Discovery look up to configure the outlook profile. Once the outlook profile configured, it will do an Auto Discovery look up to see if any changes on the Url’s or changes on the mailbox settings.

We need to know when outlook will do an Auto Discovery look up. Outlook clients automatically connect to the Autodiscover service in the following conditions:

  • When outlook client starts, both opening for the first time and every time it starts
  • Every 60 minutes once
  • Any time that the client’s connection to an Exchange Server fails

Hope this is informative J

ADRMS service provides Information Rights Management protection to Exchange Server, SharePoint Servers and File Servers. When using ADRMS, we can configure Protection Templates like Do Not Reply All, View Only etc and made them available for end users to apply those templates on email or documents to protect the confidential documents and emails.

We need to deploy ADRMS service in On-Premise environment with the required templates and need to publish those templates for end users to consume it. I have the ADMRS Infrastructure in my lab and Exchange Server 2019 installed.

Exchange Server will have the below IRM configuration as default

And users will be prompted to Connect to Rights Management Servers to get the IRM templates published by an administrator

Configuring Exchange Server 2019 to use ADRMS

Setting up Exchange Server to use IRM is simple, we need to set the InternalLicensingEnabled parameter on the Set-IRMConfiguration command to True. Below shows the settings change.

Exchange will do a SCP lookup and do the IRM configuration.

User is able to access the IRM template now after the ADRMS service deployment and the IRM configuration in Exchange.

IRM Template from OWA

I have a plan to show case the demo on IRM configuration change from ADRMS to Azure RMS for Exchange Server 2019. I will post it later.

Exchange Server 2019 automatically configures Internet Information Service Virtual Directories related to the Exchange. Clients will connect to these Virtual Directories to access the Services provided by Exchange Servers. This post shows the default configurations of Exchange Server 2019 Virtual Directory.

Internal and External URL, SSL configuration and the Authentication methods are the important parameters related to Virtual Directories, we will see all those configurations in detail.

Below are the Virtual Directory created during the Exchange Server 2019 installation.

I have preferred as the namespace for the all the exchange services and I already changed it. Exchange Certificate installation and configuration are already done.

Auto Discover:

Auto Discover allows the email clients like Outlook to discover the mailbox settings and configure the mailbox automatically without entering the details like server information etc. Service Connection Point object in AD will be referred by Auto Discover to get the User information.

Get-ClientAccessService is command to configure the Internal Url and the Authentication Methods as shown below.

No need to set the Internal / External Url using Set-AutodiscoverVirtualDirectory as it is applicable when using Exchange Server 2010.


MAPI over HTTP is the default protocol for Outlook in Exchange Server 2019 and the Exchange 2019 installation warns the MAPIHTTP enablement if it is not enabled. To ensure it is enabled, use Get-OrganizationConfig command.

Set-MapiVirtualDirectory command be used to manage MAPI over HTTP related settings

Exchange Control Panel:

Exchange Control Panel is where an admin can access Exchange Admin Center to manage the Exchange Service. Basic Authentication and FBA are the default Authentication method set on the ECP virtual directory.

Use Set-ECPVirtualDirectory command to manage the ECP virtual directory related settings.

Outlook on the Web (OWA):

OWA virtual directory allows the emails access using Web Browser and we can use Set-OWAVirtualDirectory to configure the OWA virtual directory settings

Active Sync:

Mobile Device clients that support Exchange Active Sync connects to Active Sync Virtual directory to access the mailbox.

Default configuration will not set any Authentication we can enable basic to allow the clients to access the mailbox using Active Sync protocol.

Set-ActiveSyncVirtualDirectory command allows you to configure the Active Sync related settings.

Offline Address Book (OAB):

Outlook clients using Cached mode requires offline address book to access the address book when it is not connected to exchange.

You can use Set-OABVirtualDirectory command to modify the OAB settings

Exchange Web Service (EWS):

EWS virtual directory supports many features like free busy look up, calendar sharing, mail tips and OOO etc. You can use Set-WebServicesVirtualDirectory command to manage EWS virtual directory settings.

Outlook Anywhere (OA / RPC over HTTP):

MAPI over HTTP is the default protocol for MAPI clients having mailbox in Exchange Server 2019 but it still supports Exchange for legacy clients that does not support MAPI over HTTP.

Set-OutlookAnywhere command can be used to manage Outlook Anywhere related settings.

Hope above details are informative. Comment for any queries.

S/MIME in Exchange Server 2019

December 22nd, 2018 | Posted by admin in Exchange | EXchange 2019 - (0 Comments)

Exchange Server 2019 supports sending S/MIME emails from clients like MAPI, OWA & Exchange Active Sync. We will see how to send an S/MIME email from an Exchange Server 2019 Mailbox.

S/MIME can be used to send a Signed and Encrypted email.

  • Signing an email verifies the sender and ensures the message is not changed since it was sent but it will not prevent message being read by others.
  • Encrypting the email verifies the email has not changed since it was send and it can be decrypted and read by the recipient only.

Sending S/MIME email from Exchange Server 2019 mailbox using the Internal Certificate Authority.

I have an Internal Certificate PKI already configured on my lab which allows user to enroll a User certificate that can be used to Sign and Decrypt an email.

I have select 2 mailboxes from Exchange Server 2019 to show sending and receiving S/MIME email

User Vishwa configured his outlook with a certificate which was received from Internal CA to Sign / Encrypt emails.

Sending a Signed email to Dhanyashree and she can view the Signed email.

Now Sent a Encrypted email and recipient can view those email

Below message is expected, if a user tries to send an email to another user for whom a certificate was not issued / received from CA.

Similar way, we can send S/MIME emails from OWA and Exchange Active Sync Clients. We will have a look on configuring Information Rights Management configuration in Exchange Server 2019 on my Next Post.