{"id":22369,"date":"2018-07-27T09:27:58","date_gmt":"2018-07-27T09:27:58","guid":{"rendered":"https:\/\/www.stellarinfo.com\/blog\/?p=22369"},"modified":"2025-09-12T04:34:41","modified_gmt":"2025-09-12T04:34:41","slug":"what-you-need-to-know-about-office-365-cutover-migration","status":"publish","type":"post","link":"https:\/\/www.stellarinfo.com\/blog\/what-you-need-to-know-about-office-365-cutover-migration\/","title":{"rendered":"Cutover Migration &#8211; Migrate Exchange Mailboxes to Exchange Online"},"content":{"rendered":"<?xml encoding=\"utf-8\" ?><?xml encoding=\"utf-8\" ?><p>Migrations are never an easy task and trying to migrate to Microsoft 365 or Office 365 can be hard if the end user is not keen for some downtime or some hiccups along the way. If you have an older version of Exchange like 2010 or Microsoft SBS 2011 then you need to go for the cutover migration. If you have Exchange 2007 then you will need to use IMAP migration, which in itself has some limitations. First things first, one must take precautions and a good backup of the Active Directory along with the Exchange server is to be taken. We start by creating our Microsoft 365 or Office 365 tenant and verifying the domain so that we have a good start.<\/p><p>Before starting the cutover migration configuration, make sure that the server hosting the Exchange server has been updated with the latest updates and services packs. Running the <a href=\"https:\/\/learn.microsoft.com\/en-us\/windows-server\/administration\/server-manager\/run-best-practices-analyzer-scans-and-manage-scan-results\" target=\"_blank\" rel=\"noreferrer noopener\">Best Practises Analyser<\/a> is not a requirement but it will help the process and solving unwanted issues or complications. Analyse the size of each mailbox and make sure they do not exceed the 15GB as to minimize the implications during upload or bandwidth degradation. I would suggest archiving the mailboxes to keep the last year in the mailbox. This will improve the migration process and reducing the chance of corruption or upload issues.<\/p><h2 class=\"wp-block-heading\" id=\"benefits-of-microsoft-365-migration\"><strong>Benefits of Microsoft 365 Migration<\/strong><\/h2><p>Migrating to Office 365 offers several advantages in collaboration, security, and management, apart from the financial part. With collaboration we get Microsoft Team, Co-Authoring, OneDrive, SharePoint Online and other tools that can help us work better and more secure. The security layer in the <strong>Information Rights Management (IRM)<\/strong>, <strong>Multi Factor Authentication (MFA)<\/strong>, <strong>Enterprise Mobility &amp; Security (EMS)<\/strong>, amongst others. Adding to this there is the customization of subscriptions depending on the user needs, software standardization and scalability of the tenant.<\/p><h2 class=\"wp-block-heading\" id=\"common-challenges-and-solutions\"><strong>Common Challenges and Solutions<\/strong><\/h2><p>There are several challenges before, during and after the migration. Such challenges include the setup of the licenses and what to migrate to the online platform. Sometimes the preparation work is not considered, and it could have issues on the project outcome, good preparation is key. There are other technical issues which Office 365 brings that are the data size limitations where again, preparation work needs to be done on checking public folder and mailboxes sizes to ensure that these are in line with the Office 365 limits and maybe enable archiving or split the data. Other considerations are the bandwidth that needs to be increased at the office since a lot of users are not using online services, maybe have a redundant connection, and also the user downtime, during the migration and post migration as this need to planned accordingly.<\/p><h2 class=\"wp-block-heading\" id=\"best-practices-for-exchange-server-preparation\"><strong>Best Practices for Exchange Server Preparation<\/strong><\/h2><p>Here are some of the best practices which then depending on the infrastructure and business needs.<\/p><ul class=\"wp-block-list\">\n<li>Taking stock of all the mailboxes and <strong>public folders to be migrated<\/strong> and those which will be disposed, including the size of the resources.<\/li>\n\n\n\n<li><strong>Cleanup <\/strong>the <strong>local Exchange Server<\/strong>.<\/li>\n\n\n\n<li>Decide if all the <strong>data <\/strong>will be <strong>moved<\/strong>, or a <strong>cut-off<\/strong> is decided.<\/li>\n\n\n\n<li>Keeping an inventory of all the mailboxes along with the ideal subscription assignments.<\/li>\n\n\n\n<li>Updating the <strong>Exchange Server with the latest Cumulative Update<\/strong> and <strong>operating system updates<\/strong> including any needed Service Pack updates.<\/li>\n\n\n\n<li>Running the <strong>Best practices Analyzer<\/strong>.<\/li>\n\n\n\n<li>Planning the <strong>migration <\/strong>including possible <strong>downtime<\/strong><\/li>\n<\/ul><p>Prepare the users for the new setup and offer training where needed.<\/p><h2 class=\"wp-block-heading\" id=\"mailbox-size-considerations\"><strong>Mailbox Size Considerations<\/strong><\/h2><p>Ater reviewing the mailboxes and public folders to move to Office 365, then we need to analyze and see the limitation depending on the subscription assigned to the user.<\/p><p>We need to take in consideration archiving from a particular year or the business would decide to not retain data before a particular year depending on the business, or legal obligations.&nbsp;<\/p><p>Another option would be to ask the users to cleanup their mailboxes, we all know some of the users who keep everything despite there is archiving and backups.<\/p><h2 class=\"wp-block-heading\" id=\"office-365-cutover-migration-steps\"><strong>Office 365 Cutover Migration Steps<\/strong><\/h2><ul class=\"wp-block-list\">\n<li>Sign in the <strong>Office 365 tenant<\/strong> as the <strong>Global Admin<\/strong>.<\/li>\n\n\n\n<li>Click on <strong>Setup <\/strong>and <strong>Domains <\/strong>to add your domain.<\/li>\n\n\n\n<li>After the <strong>DNS verification<\/strong>, you will be able to use the domain in the user&rsquo;s email address field.<\/li>\n\n\n\n<li>From the <strong>Exchange admin center<\/strong> in the <strong>Microsoft 365<\/strong> or <strong>Office 365<\/strong> admin portal. Click on <strong>&lsquo;Recipient&rsquo;<\/strong> and click on <strong>&lsquo;Migration&rsquo;<\/strong>. Click on the <strong>&lsquo;More&rsquo;<\/strong> button and click on <strong>&lsquo;Migration endpoints&rsquo;<\/strong>.<\/li>\n<\/ul><div class=\"wp-block-image\">\n<figure class=\"aligncenter\"><img loading=\"lazy\" decoding=\"async\" width=\"831\" height=\"278\" src=\"https:\/\/www.stellarinfo.com\/blog\/wp-content\/uploads\/2018\/07\/11.png\" alt=\"Exchange Admin center in the Microsoft 365\" class=\"wp-image-22371 apply-gradient-on-post-images\" srcset=\"https:\/\/www.stellarinfo.com\/blog\/wp-content\/uploads\/2018\/07\/11.png 831w, https:\/\/www.stellarinfo.com\/blog\/wp-content\/uploads\/2018\/07\/11-300x100.png 300w, https:\/\/www.stellarinfo.com\/blog\/wp-content\/uploads\/2018\/07\/11-768x257.png 768w\" sizes=\"auto, (max-width: 831px) 100vw, 831px\" \/><\/figure>\n<\/div><ul class=\"wp-block-list\">\n<li>Click on the<strong> &lsquo;+&rsquo; Sign<\/strong> to create the new endpoint and in the first screen tick <strong>&lsquo;Outlook Anywhere&rsquo;<\/strong>, Click Next.<\/li>\n<\/ul><div class=\"wp-block-image\">\n<figure class=\"aligncenter\"><img loading=\"lazy\" decoding=\"async\" width=\"538\" height=\"395\" src=\"https:\/\/www.stellarinfo.com\/blog\/wp-content\/uploads\/2018\/07\/12.png\" alt=\"New Migration Endpoint window\" class=\"wp-image-22372 apply-gradient-on-post-images\" srcset=\"https:\/\/www.stellarinfo.com\/blog\/wp-content\/uploads\/2018\/07\/12.png 538w, https:\/\/www.stellarinfo.com\/blog\/wp-content\/uploads\/2018\/07\/12-300x220.png 300w\" sizes=\"auto, (max-width: 538px) 100vw, 538px\" \/><\/figure>\n<\/div><ul class=\"wp-block-list\">\n<li>In the next screen, you will be prompted to enter the &rsquo;email address&rsquo; of one of the mailboxes to be imported and the domain account name and password of a user who has administrative privileges on the Exchange server.<\/li>\n\n\n\n<li>To confirm the endpoint you will need to enter the FQDN which is hosting the Exchange server and the RPC Proxy server which in most instances would be the same as the Exchange Server.<\/li>\n\n\n\n<li>Here is the tricky part, you must make sure that Outlook Anywhere is working successfully and without any issues.<\/li>\n<\/ul><div class=\"wp-block-image\">\n<figure class=\"aligncenter\"><img loading=\"lazy\" decoding=\"async\" width=\"498\" height=\"288\" src=\"https:\/\/www.stellarinfo.com\/blog\/wp-content\/uploads\/2018\/07\/13.png\" alt=\"Stellar\" class=\"wp-image-22373 apply-gradient-on-post-images\" srcset=\"https:\/\/www.stellarinfo.com\/blog\/wp-content\/uploads\/2018\/07\/13.png 498w, https:\/\/www.stellarinfo.com\/blog\/wp-content\/uploads\/2018\/07\/13-300x173.png 300w\" sizes=\"auto, (max-width: 498px) 100vw, 498px\" \/><\/figure>\n<\/div><ul class=\"wp-block-list\">\n<li>After the verification, you will have the Microsoft 365 or Office 365 connected to your Exchange Server. Now, on the Migration screen click on the &lsquo;+&rsquo; sign and click on <strong>&lsquo;Migrate to Exchange Online&rsquo;<\/strong>.<\/li>\n<\/ul><div class=\"wp-block-image\">\n<figure class=\"aligncenter\"><img loading=\"lazy\" decoding=\"async\" width=\"746\" height=\"300\" src=\"https:\/\/www.stellarinfo.com\/blog\/wp-content\/uploads\/2018\/07\/15.png\" alt=\"Migration screen in Office 365 connected to your Exchange Server\" class=\"wp-image-22374 apply-gradient-on-post-images\" srcset=\"https:\/\/www.stellarinfo.com\/blog\/wp-content\/uploads\/2018\/07\/15.png 746w, https:\/\/www.stellarinfo.com\/blog\/wp-content\/uploads\/2018\/07\/15-300x121.png 300w\" sizes=\"auto, (max-width: 746px) 100vw, 746px\" \/><\/figure>\n<\/div><p>After going through the rest of the wizard and entering the required details and credentials, the data will start to copy. After some time, you can go to the same screen and check the progress. If all goes well, you will get the status of the mailboxes as Synced and the initial synchronization is completed.<\/p><p>From this moment, you can cut over the DNS records and assign the licenses to your users. From the Active users, you can either assign the licenses one by one if you have mix of E3, Business Essentials or Premium or by using the bulk actions for the users.<\/p><ul class=\"wp-block-list\">\n<li>To change the <strong>DNS records<\/strong>, you must open the domains from the <strong>setup menu<\/strong> on the left sidebar.<\/li>\n<\/ul><div class=\"wp-block-image\">\n<figure class=\"aligncenter\"><img loading=\"lazy\" decoding=\"async\" width=\"508\" height=\"280\" src=\"https:\/\/www.stellarinfo.com\/blog\/wp-content\/uploads\/2018\/07\/16.png\" alt=\"Stellar\" class=\"wp-image-22375 apply-gradient-on-post-images\" srcset=\"https:\/\/www.stellarinfo.com\/blog\/wp-content\/uploads\/2018\/07\/16.png 508w, https:\/\/www.stellarinfo.com\/blog\/wp-content\/uploads\/2018\/07\/16-300x165.png 300w\" sizes=\"auto, (max-width: 508px) 100vw, 508px\" \/><\/figure>\n<\/div><p>You will be required to enter the additional DNS record with your DNS provider, which are given by the portal in the page. If you want, you can either choose to go with your own DNS provider of use the Microsoft 365 or Office 365 DNS facility which mind you, you still need a DNS provider for the first verification process of the domain, afterwards you can disable it and route the Name Servers (NS) to Microsoft 365 or Office 365 directly.<\/p><p>After adding the DNS entries please note that due to the global DNS propagation, the change to be reflected everywhere it can take up to 24 hours. This may cause some delivery issues during the period and some emails can be delayed but unfortunately, it&rsquo;s part of the migration headaches.<\/p><p>From here onwards, you can say to the users that they can work on their new mailboxes using mobile and web access. For the local users you need to make sure that any DNS entries pointing to the internet domain are updated. After Exchange has been uninstalled from the server you must make sure that any Autodiscover entries are removed and a new CNAME records has been created which is pointing the Autodiscover. to <strong>Autodiscover.outlook.com<\/strong> like below. Also, you must be sure that there are no records which are left there from the uninstall which can cause issues with Autodiscover service, so make sure that you clean up your Active Directory Schema after the uninstall.<\/p><div class=\"wp-block-image\">\n<figure class=\"aligncenter\"><img loading=\"lazy\" decoding=\"async\" width=\"559\" height=\"290\" src=\"https:\/\/www.stellarinfo.com\/blog\/wp-content\/uploads\/2018\/07\/17.png\" alt=\"Stellar\" class=\"wp-image-22376 apply-gradient-on-post-images\" srcset=\"https:\/\/www.stellarinfo.com\/blog\/wp-content\/uploads\/2018\/07\/17.png 559w, https:\/\/www.stellarinfo.com\/blog\/wp-content\/uploads\/2018\/07\/17-300x156.png 300w\" sizes=\"auto, (max-width: 559px) 100vw, 559px\" \/><\/figure>\n<\/div><p>Once complete this can be tested by opening a command prompt and trying to ping the <strong>autodiscoverAutodiscover.<\/strong>. If it does not work or it is not pointing to the right IP, then run <strong>ipconfig \/flushdns<\/strong> and retry.<\/p><div class=\"wp-block-image\">\n<figure class=\"aligncenter\"><img loading=\"lazy\" decoding=\"async\" width=\"947\" height=\"247\" src=\"https:\/\/www.stellarinfo.com\/blog\/wp-content\/uploads\/2018\/07\/18.png\" alt=\"Stellar\" class=\"wp-image-22377 apply-gradient-on-post-images\" srcset=\"https:\/\/www.stellarinfo.com\/blog\/wp-content\/uploads\/2018\/07\/18.png 947w, https:\/\/www.stellarinfo.com\/blog\/wp-content\/uploads\/2018\/07\/18-300x78.png 300w, https:\/\/www.stellarinfo.com\/blog\/wp-content\/uploads\/2018\/07\/18-768x200.png 768w\" sizes=\"auto, (max-width: 947px) 100vw, 947px\" \/><\/figure>\n<\/div><p>Although it will say Request timed out, you must make sure that it resolved correct to the onmicrosoft domain.office.com. Once this is ready you may go ahead to setup your local Outlook to connect via Microsoft 365 or Office 365. Better said than done as if all goes well and your setup is impeccable, you will have a clean migration, but it can get tricky when it comes to those pesky issues that return misleading error message.<\/p><p>As said in my first paragraph you can say that the above will not work on your Exchange 2003 and below. For that, you would need to use the IMAP migration as contacts, calendar items or task will not be migrated and you would have to export and import these through Outlook. You can migrate up to 500,000 items per user mailbox and each email must not be larger than 35MB. Of course, with IMAP migration you would need either to know the password for the users&rsquo; mailboxes or reset them, which would create an impact on your users.<\/p><h2 class=\"wp-block-heading\" id=\"post-migration-cleanup-and-validation\"><strong>Post-Migration Cleanup and Validation<\/strong><\/h2><p>Once the migration is complete, one can go ahead with the post migration tasks. First, we need to ensure that one last backup was taken of the Exchange Server. The next thing is to remove all the mailboxes from the Exchange Server as well as the system mailboxes. After this step we can go ahead and uninstall the Exchange Server. Why is this needed? The configuration of all the Exchange Server is stored in the Active Directory Schema and there are a lot of changes in the schema which relate to Exchange Server. So, just shutting down the Exchange Server and <a href=\"https:\/\/www.stellarinfo.com\/blog\/how-to-decommission-exchange-server-after-migration-to-office-365\/\" target=\"_blank\" rel=\"noreferrer noopener\">decommissioning the Exchange Server<\/a> would mean that these parameters are not cleaned which could lead to routing and other problems. After the above is complete, one can easily decommission the Operating system and server.<\/p><h2 class=\"wp-block-heading\" id=\"conclusion\"><strong>Conclusion<\/strong><\/h2><p>On the other hand, during migrations and post-migration, the first priority is always to ensure minimal impact on end users and to reduce the chances of administrative errors from the sysadmin side. Additionally, if any mailbox is missed or if historic emails need to be retrieved from the source server, this can be a challenge with native options.<\/p><p><strong><a href=\"https:\/\/www.stellarinfo.com\/exchange-migration.php\">Stellar Migrator for Exchange<\/a><\/strong> simplifies this process. The tool is quick to install, lightweight, yet very powerful. It allows direct and seamless migration of primary mailboxes, archives, and public folders from on-premises Exchange to Office 365 or another Exchange environment.<\/p><p>With features like <strong>automatic mailbox mapping, parallel mailbox migrations, priority settings for VIP users, and staged migration support<\/strong>, administrators can carry out the migration with ease and peace of mind. Post-migration, the tool also supports re-migration and delta migration to ensure no data is missed.<\/p><h2 class=\"wp-block-heading\" id=\"faq\"><strong>FAQ<\/strong><\/h2>\n","protected":false},"excerpt":{"rendered":"<p>Migrations are never an easy task and trying to migrate to Microsoft&hellip; <a class=\"more-link\" href=\"https:\/\/www.stellarinfo.com\/blog\/what-you-need-to-know-about-office-365-cutover-migration\/\">Continue reading <span class=\"screen-reader-text\">Cutover Migration &#8211; Migrate Exchange Mailboxes to Exchange Online<\/span><\/a><\/p>\n","protected":false},"author":7,"featured_media":7426,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"_acf_changed":false,"footnotes":""},"categories":[2960],"tags":[],"class_list":["post-22369","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-migrate-to-office-365","entry"],"acf":[],"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v26.9 - https:\/\/yoast.com\/product\/yoast-seo-wordpress\/ -->\n<title>Cutover Migration - Migrate Exchange Mailboxes to Exchange Online<\/title>\n<meta name=\"description\" content=\"Move Exchange mailboxes to the Office 365 or Exchange Online seamlessly with Cutover Migration Step by Step Guide.\" \/>\n<meta name=\"robots\" content=\"index, follow, max-snippet:-1, max-image-preview:large, max-video-preview:-1\" \/>\n<link rel=\"canonical\" href=\"https:\/\/www.stellarinfo.com\/blog\/what-you-need-to-know-about-office-365-cutover-migration\/\" \/>\n<meta property=\"og:locale\" content=\"en_US\" \/>\n<meta property=\"og:type\" content=\"article\" \/>\n<meta property=\"og:title\" content=\"Cutover Migration - Migrate Exchange Mailboxes to Exchange Online\" \/>\n<meta property=\"og:description\" content=\"Move Exchange mailboxes to the Office 365 or Exchange Online seamlessly with Cutover Migration Step by Step Guide.\" \/>\n<meta property=\"og:url\" content=\"https:\/\/www.stellarinfo.com\/blog\/what-you-need-to-know-about-office-365-cutover-migration\/\" \/>\n<meta property=\"og:site_name\" content=\"Stellar Data Recovery Blog\" \/>\n<meta property=\"article:published_time\" content=\"2018-07-27T09:27:58+00:00\" \/>\n<meta property=\"article:modified_time\" content=\"2025-09-12T04:34:41+00:00\" \/>\n<meta property=\"og:image\" content=\"https:\/\/www.stellarinfo.com\/blog\/wp-content\/uploads\/2017\/05\/2-2.jpg\" \/>\n\t<meta property=\"og:image:width\" content=\"1000\" \/>\n\t<meta property=\"og:image:height\" content=\"600\" \/>\n\t<meta property=\"og:image:type\" content=\"image\/jpeg\" \/>\n<meta name=\"author\" content=\"Eric Simson\" \/>\n<meta name=\"twitter:card\" content=\"summary_large_image\" \/>\n<meta name=\"twitter:label1\" content=\"Written by\" \/>\n\t<meta name=\"twitter:data1\" content=\"Eric Simson\" \/>\n\t<meta name=\"twitter:label2\" content=\"Est. reading time\" \/>\n\t<meta name=\"twitter:data2\" content=\"10 minutes\" \/>\n<script type=\"application\/ld+json\" class=\"yoast-schema-graph\">{\"@context\":\"https:\/\/schema.org\",\"@graph\":[{\"@type\":\"Article\",\"@id\":\"https:\/\/www.stellarinfo.com\/blog\/what-you-need-to-know-about-office-365-cutover-migration\/#article\",\"isPartOf\":{\"@id\":\"https:\/\/www.stellarinfo.com\/blog\/what-you-need-to-know-about-office-365-cutover-migration\/\"},\"author\":{\"name\":\"Eric Simson\",\"@id\":\"https:\/\/www.stellarinfo.com\/blog\/#\/schema\/person\/b4823430443e4bb02f48d6dfaad50f89\"},\"headline\":\"Cutover Migration &#8211; 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