Refer to this article to guide the customers in answering the Migration Discovery Questions, and to provide an explanation as to why these questions are asked before setting up a migration project. 

Email Environment

1) In total, how many mailboxes does your company need to migrate ?

You need to make sure the number of mailboxes matches the number of migration licenses purchased. If it doesn’t match, escalate to the Partner so they can update the number of migration seats.

You will also determine the type of migration, whether Staged or Cutover, based on the total number of mailboxes being migrated. For example, cutover migrations are ideal for up to 250 licenses, anything above this number should be treated as a Staged migration (listed under SkyKick Enterprise Planner).

During the Migration Planner phase, you will need to gather a list of all of their shared mailboxes, shared calendars and public folders. You must also educate them about the public folder limits outlined below and set the right expectations with them.

Refer to the following SkyKick articles for more information (requires you to log in to SkyKick to access the articles):

• How to streamline the migration of large Public Folders
• Configuring Public Folders

2) Enter an example of an email address your company would like to migrate.

For example, john.travolta@contoso.com should correspond to the SMTP for this company's end user as listed in the primary domain provided by the customer.

3) Where are you migrating your email data from? (e.g. Hosted Exchange, Google, IMAP, Microsoft 365)

For Google Workspace:
If the answer is Google, note that Google requires extra security measures to be in place (2-step verification and temporary app account credentials in Gmail) + Google Service account creation for the migration to take place. Refer to this article from Microsoft called
Prepare your Gmail or Google Workspace (formerly G Suite) account for connecting to Outlook and Microsoft 365 or Office 365.

To get the Google APIs required to access mailbox data on behalf of users, an administrator of the Google Apps domain must create a Service Account and provide the details of that account to the Migration Planner. To get started, see this article from SkyKick called How to create a Google Apps Service Account (requires you to log in to SkyKick to access the article).

For Hosted Exchange considerations:
Check if Source-Side Impersonation (SSI) is supported by referring to this article from SkyKick called
Migrating to Office 365 from a hosted email environment (requires you to log in to SkyKick to access the article).

4) Where would you like to migrate your emails (e.g. Microsoft 365 or Google Workspace)?

For M365- to-M365 / tenant to tenant:
If migrating from Microsoft 365 to Microsoft 365, there are special considerations as listed in this article from SkyKick called Planning and Managing an Office 365 to Office 365 Migration (requires you to log in to SkyKick to access the article).

For Google to Google:
If Migrating from Google Workspace to Google Workspace, DMS can be used for up to 100 users. Refer to this article from Google called Migrate email with the data migration service.

Also see all necessary considerations when migrating from Google to M365 by referring to this article from SkyKick called Google Migrations - What you need to know (requires you to log in to SkyKick to access the article).

5) Does your company use any Macs, Windows Vista or any older operating systems? If yes, please list how many for each.

This question serves to determine what type of computers are supported and which aren’t when discussing OA deployment pre-requisites with customer:

• Outlook Assistant is NOT supported on Mac or terminal server.
• Outlook Assistant from SkyKick only works on newer versions of Windows.

If the POC has Macs or has Windows Vista (or an older operating system), inform them that end users will need to set up their email using Outlook, Mac Mail or anything else manually. You can provide knowledge base articles to support them with this.

What local data and settings is the Outlook Assistant designed to migrate?

• Signature blocks
• Address autocomplete (NK2 file)
• Re-attaches to the new profile any offline PSTs that are stored at:
  Local Disk (C:) > Users > [User account] > AppData > Local > Microsoft > Outlook

6) Which email software does your company use  (e.g. Outlook, Webmail, Thunderbird)?

You need to inquire about the local email client used in the customer’s desktop environment and its version to determine if it is supported or out of scope.

If Outlook, what version? You will need to explain that Outlook 2007 for example will need to be set up manually as it isn’t supported with SKOA.

NOTE: Outlook Assistant is NOT supported on Macs or terminal servers.

7) Does your company have any applications or devices that require a mailbox or messaging service (e.g. printer server, terminal server,  CRM, projector, meeting room, audio/video device or other resource)? If yes, please list how many for each.

If the answer is Yes, ask the customer to list the device type, name & mailbox address. You will only create a destination mailbox as specified by POC and migrate any email data from source to destination mailbox.

This question is intended to determine any device or application that uses the mail server. The reason you ask this is to avoid post-migration issues related to it. For example, printers not sending emails after the migration. Though they are out of scope, you can still point the POC in the right direction on how to set these up in their M365 or Google environments after migrating over. You must also set the right expectations with the POC from the get go regarding the fact that you cannot configure these for them, but you can provide best effort support only.

IMPORTANT NOTE:
All thin devices such as a VM, Terminal server, CRM etc. and/or actual hardware such as Multi-function printers, print servers, or other equipment are NOT supported by SkyKick and will require a manual configuration by the customer.

All other configurations are out of scope. You can point the customer to Microsoft/Google KB as a courtesy and should redirect them back to their local IT or Partner support for additional troubleshooting or configuration questions on such applications/devices.

8) Do you have any public folders, shared mailboxes/calendars, distribution groups, or conference room mailboxes that need to be migrated? If yes, please list them or type N/A if not applicable. 

You must gather all of the different public folders and shared calendars from the POC and enter that information in the SkyKick Migration Planner during the Phase 3 (Migration Planner call) under the Review Accounts section.

IMPORTANT NOTE:

• Shared mailboxes in M365 = No license needed
• Public Folders = Exchange Online or Business license needed
• Folder-Level Permissions are necessary for successful Public Folder migration:
  • In order to migrate public folders to or from Office 365, it is necessary to grant administrator account root-level permissions to public folders. This works best for migrations of under a thousand folders, otherwise this process should be done with PowerShell. 
  • Folder-level permissions can be assigned to any folder within a mailbox or Public Folder (e.g. inbox, calendar, contacts, etc.). SkyKick Server Sync will collect these permissions in Exchange via EWS and will attempt to replicate these on the mailbox or Public Folder in the destination Office 365 tenant. 
  • If a permission is found for an object on source that does not have a corresponding email address in Office 365, the permission will not be applied to the folder in Office 365.

9) What type of anti-spam services setup does your company use?

The reason you ask this is because you need to rule out if the POC has any spam filters that may impact discovery and other configuration options, such as DNS automation options. For example, if Spam filters are in place, Manual DNS option will be required instead of Partial/Semi-Assisted.

If this is “Yes”, advise the POC to inform their anti-spam service about the migration to ensure that any configurations stay intact.

10) Do you know your administrator credentials for your new email platform?

If “No”, ask the POC if they received a welcome email from the new platform (e.g. search for Microsoft or Google Workspace in their inbox). If they did not receive an email, escalate to the Partner.

11) Do you have any inbox rules or server-side rules that you would like to import during the migration?

Server-Side:
We do not support server-side rules except the following scenario. If the answer is “Yes”, the only supported server-side rules with Exchange/SkyKick are conditions and actions handled by the Exchange server. For example, from <people or distribution list in the GAL or your contacts list>, move it to the <specified> folder.

Inbox Rule Migration:
The vast majority of Inbox Rules are server-side rules. These can only be migrated from Exchange 2010 SP1 or newer. This option appears for most users on the Final Review page of the Migration Planner and needs to be requested from SkyKick support to display in the Planner.

IMPORTANT: Users may also have client-side rules which will still need to be recreated manually following the migration. For more information, refer to this article from Microsoft called Client-side vs. server-side rules.

Also, below is a simple way to identify any rules which are client-side.

12) Do you have any mailboxes that are above or close to 20GB in size? If yes, list all applicable email addresses.

If this is “Yes”, you will need to ask the POC during the Migration Planner phase for more details about the associated user accounts that have massive mailboxes near or above > 20GB which is in the danger zone and advise them on cleaning up/reducing large mailbox size over that 20 GB threshold (which is the acceptable mailbox size) in accordance with the official Exchange Online Limits and discuss the allowed:

• Mailbox Folder Limits
• Recommended Mailbox Size Limits
• Exchange Online limits - Service Descriptions

Out of Scope

If POC insists on keeping them over this threshold, then they must be made aware that this will be considered Out of Scope as it will very likely cause huge delays, if not migration failure for the affected mailboxes.

Ideally, they should run a ScanPST on their source PST files and let the tool repair any corruptions, errors and fragmentation.

Other important considerations/expectations include:

• Large item count (number of emails and calendar events > 1000 000+),

• Folder/subfolder hierarchy depth > 300 for individual mailboxes,

• Large email attachments

• Emails dating from over 1 year (default Cached Exchange Mode rule preset to display emails from the last 6 months or 1 year only). Extending Cached Mode to All time or several years back should fix the issue but may take hours or days to populate.

• The recommended action would be to recreate a new profile and follow official Microsoft recommendations by referring to this article called
  Outlook performance issues when there are too many items or folders in a cached mode .ost or .pst file.

Expectations to explain to customer about excessively high item count and complex folder hierarchy:

It's not the size of the mailbox that impacts performance - it is the number of items in the folder or folders that are being accessed on the server.  In particular, performance is largely influenced by the number of items in the most commonly used folders: Calendar, Contacts, Inbox, and Sent Item folder. 

Having a large number of item count in a folder will mean than operations in that folder will take longer.  Operations that depend on the number of items in the folder include adding a new column to the view, sorting on a new column, finds and searches. Many Outlook plug-ins do sorts or searches as they are running, and these requests may overlap with other Outlook MAPI requests, resulting in a poor user experience.

13) Do you have any users that have more than one PC or more than one mailbox?

During the Migration Planner call, this question helps you identify the number of PCs that will require an Outlook Assistant deployment, which ones should NOT have Outlook Assistant installed (per the POC) and which are terminal servers for example and how many separate profiles will be configured on a user’s local Outlook client.

14) Please list the accounts and names of executive users and Core IT staff users.

It’s important to identify the different departments and their respective users, especially mission critical IT and VIP/executive teams to cautiously plan those individually and/or to make sure any special configurations are addressed as soon as possible.

15) Do you have any forwarding or special mail flow rules enabled for your domain?

This question is necessary to allow you to set the proper expectations about what is IN scope and what is out of scope during the Migration Planning call that follows the order placement.

Domain Information

16) Which domain(s) are you looking to migrate? Please specify if you are planning to migrate to a domain name that is different than your current primary domain. For example, from contoso.net to domain.com. 

During the Migration Planner phase, you must ask them additional information by having the POC list all of their subdomains and domain aliases and specify their primary source and its destination domain names.
If customer is looking to migrate from multiple primary source domains, then you must point them to consider multiple migration projects for each source domain. This only applies for PRIMARY domains. Aliases or secondary domains can be migrated in the same migration project.

17) Who is your domain registrar?

If the POC doesn’t know their domain registrar, you can help them use the WHOIS tool to find out.

18) Are you the administrator for your domain registrar?

If this is “Yes”, ask the POC to test their credentials to confirm that they do have access.

If this is “No”, ask them to put you through to their domain owner/administrator so they can provide us with their administrator login credentials. Otherwise, guide the customer to contact their domain registrar, if they no longer recall their login information or have no domain admin.

19) Do you have an Active Directory on-premises

If this is “Yes”, you will need to ask the POC for more details about the active directory setup during the Migration Planner phase. For example, find out if they plan on synchronizing some accounts via ADSync for a hybrid setup.

20) Does your company have a website running on Active Directory?

This question is intended to ensure business continuity of the POC’s services, including their website if it's running off of their AD server.