{"id":121,"date":"2019-05-04T15:27:07","date_gmt":"2019-05-04T13:27:07","guid":{"rendered":"https:\/\/greg.klonis.gr\/?p=121"},"modified":"2021-09-23T10:32:36","modified_gmt":"2021-09-23T08:32:36","slug":"upgrade-to-windows-server-2019","status":"publish","type":"post","link":"https:\/\/greg.klonis.gr\/index.php\/upgrade-to-windows-server-2019","title":{"rendered":"Upgrade to Windows Server 2019"},"content":{"rendered":"\n<h2 class=\"wp-block-heading\"> Pre-Upgrade <\/h2>\n\n\n\n<hr class=\"wp-block-separator\"\/>\n\n\n\n<h3 class=\"wp-block-heading\">Upgrade path:<\/h3>\n\n\n\n<blockquote class=\"wp-block-quote is-layout-flow wp-block-quote-is-layout-flow\"><p>Windows Server 2008 R2 can be upgraded to Windows Server 2019 in \nthree consecutive upgrade processes &#8211; first by upgrading to Windows \nServer 2012, and then upgrading Windows Server 2012 to Windows Server \n2016, and then upgrading from Windows Server 2016 to Windows Server \n2019.<\/p><\/blockquote>\n\n\n\n<h3 class=\"wp-block-heading\">Support:<\/h3>\n\n\n\n<blockquote class=\"wp-block-quote is-layout-flow wp-block-quote-is-layout-flow\"><p>In-place Upgrade is supported for Windows Server versions 2008 R2, \n2012 R2 and 2016 on physical hardware, and in Virtual Machines. Public \nand private cloud companies also support In-place Upgrade of Windows \nServer versions 2008 R2, 2012 and 2016 Virtual Machines \u2013 check with \nyour cloud provider.<\/p><\/blockquote>\n\n\n\n<h3 class=\"wp-block-heading\">Alternative:<\/h3>\n\n\n\n<blockquote class=\"wp-block-quote is-layout-flow wp-block-quote-is-layout-flow\"><p>Migrate (re-deploy) applications and data on a clean install of Windows Server 2019.<\/p><\/blockquote>\n\n\n\n<h3 class=\"wp-block-heading\">Limitations:<\/h3>\n\n\n\n<blockquote class=\"wp-block-quote is-layout-flow wp-block-quote-is-layout-flow\"><p>Windows Servers configured to \u201cBoot from VHD\u201d cannot be upgraded using In-place Upgrade.<\/p><\/blockquote>\n\n\n\n<!--more-->\n\n\n\n<h2 class=\"wp-block-heading\">Planning for In-place Upgrade<\/h2>\n\n\n\n<hr class=\"wp-block-separator\"\/>\n\n\n\n<p>Before proceeding with In-place Upgrade, collect the following information:<\/p>\n\n\n\n<ul class=\"wp-block-list\"><li>Is there a target or goal timeframe for upgrading this server?\n<\/li><li>Is this a production-critical server?\n<\/li><li>Is there a maintenance window for upgrading this server?\n<\/li><li>Is there enough time for a test upgrade on an identical or similar non-production server?\n<\/li><li>Who uses this server? Internal users, external users, or both? Have they been informed of the upgrade or maintenance?\n<\/li><li>Is there an inventory of what is running on the server? Check the following:\n<ul><li>Windows Server Roles and Features\n<\/li><li>Microsoft applications: SQL Server, SharePoint Server, Exchange Server, etc.\n<\/li><li>3rd-Party applications: SAP, Oracle, DB2, etc.\n<\/li><li>Is the server joined to an Active Directory domain?\n<\/li><li>Are any of the server disks BitLocker protected?\n<\/li><li>Is the server part of a Failover Cluster? Note that Failover Clusters have separate migration options.\n<\/li><\/ul>\n<\/li><li>How often is the server backed-up? Have backups ever been successfully restored (applied) to the server or applications?\n<\/li><li>What backup software is used?\n<\/li><li>If In-place Upgrade is not successful and the server needs to be \nrebuilt, are the Windows Server and application install media available?\nAlthough it is rare, In-place Upgrade can fail and there should be a \nplan in-place for this possibility, to minimize server downtime and \nmaintain SLAs.\n<\/li><li>Is the server fully patched? It is strongly recommended that the server is fully patched prior to In-place Upgrade.\n<\/li><li>Run <strong>systeminfo.exe<\/strong> and save the output:\n\n<\/li><\/ul>\n\n\n\n<ul class=\"wp-block-list\"><li>Run <strong>ipconfig \/all<\/strong> and save the output:\n\n<\/li><\/ul>\n\n\n\n<ul class=\"wp-block-list\"><li>Use the Server Manager to list the Roles and Features installed on the server.\n<\/li><li>Run <strong>RegEdit<\/strong> and capture the value of the the\n<strong>HKEY_LOCAL_MACHINE\\SOFTWARE\\Microsoft\\WindowsNT\\CurrentVersion<\/strong> hive \u2013 this will show the exact version (<strong>BuildLabEx<\/strong>) and edition (<strong>EditionID<\/strong>) of Windows Server:\n\n<\/li><\/ul>\n\n\n\n<h2 class=\"wp-block-heading\">Before proceeding with the In-place Upgrade<\/h2>\n\n\n\n<hr class=\"wp-block-separator\"\/>\n\n\n\n<ol class=\"wp-block-list\"><li>Backup the Operating System, Applications, and Virtual Machines.\n<\/li><li>Shutdown, Quick Migrate, or Live Migrate all Virtual Machines running on the server &#8211; Virtual Machines <strong>cannot<\/strong> be running on the server during In-place Upgrade.\n<\/li><\/ol>\n\n\n\n<h2 class=\"wp-block-heading\"> Upgrade <\/h2>\n\n\n\n<h2 class=\"wp-block-heading\">1 of 3: Windows Server 2008 R2 to Windows Server 2012<\/h2>\n\n\n\n<hr class=\"wp-block-separator\"\/>\n\n\n\n<ol class=\"wp-block-list\"><li>Locate the setup media for Windows Server 2012\n<\/li><li>Run <strong>setup.exe<\/strong> by double-clicking it:\n\n<\/li><\/ol>\n\n\n\n<ol class=\"wp-block-list\"><li>Click <strong>Yes<\/strong> to enable setup to proceed:\n\n<\/li><\/ol>\n\n\n\n<ol class=\"wp-block-list\"><li>Click <strong>Install now<\/strong>:\n\n<\/li><\/ol>\n\n\n\n<ol class=\"wp-block-list\"><li>For internet-connected devices, click <strong>Go online to install updates now:<\/strong>\n\n<\/li><\/ol>\n\n\n\n<ol class=\"wp-block-list\"><li>You will be prompted to select the image of the Edition to upgrade to. Then click <strong>Next<\/strong>:\n\n<\/li><\/ol>\n\n\n\n<ol class=\"wp-block-list\"><li>Depending on the distribution channel that you received Windows \nServer media from (Retail, Volume License, OEM, ODM, etc.) you may be \npresented with different license agreements. Click \u201c<strong>I accept the license terms<\/strong>\u201d and then click <strong>Next<\/strong>:\n\n<\/li><\/ol>\n\n\n\n<ol class=\"wp-block-list\"><li>For In-place Upgrade, select <strong>Upgrade: Install Windows and keep files, settings, and applications:<\/strong>\n\n<\/li><\/ol>\n\n\n\n<ol class=\"wp-block-list\"><li>Setup will remind you to check application compatibility \u2013 click <strong>Next<\/strong>:\n\n<\/li><\/ol>\n\n\n\n<ol class=\"wp-block-list\"><li>In the Windows Server 2016 setup.exe, one page says that upgrade is \nnot recommended, in order to encourage customers to prefer clean \ninstall.<\/li><\/ol>\n\n\n\n<blockquote class=\"wp-block-quote is-layout-flow wp-block-quote-is-layout-flow\"><p>Note this page has been removed from Windows Server 2019 setup.exe. Press <strong>Confirm<\/strong>:<\/p><\/blockquote>\n\n\n\n<figure class=\"wp-block-image\"><img decoding=\"async\" src=\"https:\/\/raw.githubusercontent.com\/coreyp-at-msft\/ws-upgrade-center\/dev\/en-US\/media\/550118726813c1bad7c825eb87f4d70c.png\" alt=\"\"\/><\/figure>\n\n\n\n<ol class=\"wp-block-list\"><li>Setup will complete and the server will reboot.<\/li><\/ol>\n\n\n\n<h2 class=\"wp-block-heading\">Post Upgrade: Windows Server 2012<\/h2>\n\n\n\n<hr class=\"wp-block-separator\"\/>\n\n\n\n<ol class=\"wp-block-list\"><li>After Setup has completed installing and rebooted the sever, \nlogin to check that the server has been successfully upgraded. If you \nselected Windows Server 2012 Standard or Datacenter Desktop Edition, you\n should see the Server Manager window:\n\n<\/li><\/ol>\n\n\n\n<ol class=\"wp-block-list\"><li>Run <strong>RegEdit<\/strong> and check the value of the <strong>HKEY_LOCAL_MACHINE\\SOFTWARE\\Microsoft\\WindowsNT\\CurrentVersion<\/strong> hive \u2013 the version should be successfully updated to Windows Server 2012.\n\n<\/li><\/ol>\n\n\n\n<ol class=\"wp-block-list\"><li>Check that applications are running and that client connections to the applications succeed.\n<\/li><li>If you believe that there has been an issue upgrading you server, you should copy and Zip the <strong>%SystemRoot%\\Panther<\/strong> (usually <strong>C:\\Windows\\Panther<\/strong>) directory and contact support.\n<\/li><\/ol>\n\n\n\n<h2 class=\"wp-block-heading\">Upgrade 2 of 3: Windows Server 2012 to Windows Server 2016<\/h2>\n\n\n\n<hr class=\"wp-block-separator\"\/>\n\n\n\n<ol class=\"wp-block-list\"><li>Patch the server. It is strongly recommended that the server is \nfully patched, even if your previous Windows Server 2008 R2 was fully \npatched.\n<\/li><li>Backup the Operating System, Applications, and Virtual Machines.\n<\/li><li>Locate the setup media for Windows Server 2016\n<\/li><li>Run <strong>setup.exe<\/strong> by double-clicking it:\n\n<\/li><\/ol>\n\n\n\n<ol class=\"wp-block-list\"><li>Click <strong>Yes<\/strong> to enable setup to proceed:\n\n<\/li><\/ol>\n\n\n\n<ol class=\"wp-block-list\"><li>For internet-connected devices, we recommend the <strong>Download updates, drivers and optional features option<\/strong>. Click <strong>Next<\/strong>:\n\n<\/li><\/ol>\n\n\n\n<ol class=\"wp-block-list\"><li>Setup will check the configuration of your computer \u2013 please wait:\n\n<\/li><\/ol>\n\n\n\n<ol class=\"wp-block-list\"><li>Depending on the distribution channel that you received Windows \nServer media from (Retail, Volume License, OEM, ODM, etc.) and the \nlicense for the server, you may be prompted to enter a licensing key to \nproceed:\n\n<\/li><\/ol>\n\n\n\n<ol class=\"wp-block-list\"><li>You will be prompted to select the image of the Edition to upgrade to. Then click <strong>Next<\/strong>:\n\n<\/li><\/ol>\n\n\n\n<ol class=\"wp-block-list\"><li>Depending on the distribution channel that you received Windows \nServer media from (Retail, Volume License, OEM, ODM, etc.) you may be \npresented with different license agreements. click <strong>Accept<\/strong>:\n\n<\/li><\/ol>\n\n\n\n<ol class=\"wp-block-list\"><li>For In-place Upgrade, select <strong>Keep personal files and apps<\/strong>, and then click <strong>Next<\/strong>:\n\n<\/li><\/ol>\n\n\n\n<ol class=\"wp-block-list\"><li>In the Windows Server 2016 setup.exe, one page says that upgrade is \nnot recommended, in order to encourage customers to prefer clean \ninstall.<\/li><\/ol>\n\n\n\n<blockquote class=\"wp-block-quote is-layout-flow wp-block-quote-is-layout-flow\"><p><strong>Note:<\/strong> this pages has been removed from Windows Server 2019 setup.exe. Press <strong>Confirm<\/strong>:<\/p><\/blockquote>\n\n\n\n<figure class=\"wp-block-image\"><img decoding=\"async\" src=\"https:\/\/raw.githubusercontent.com\/coreyp-at-msft\/ws-upgrade-center\/dev\/en-US\/media\/9a877f6eef7ced554fb1b6e613eb70d6.png\" alt=\"\"\/><\/figure>\n\n\n\n<ol class=\"wp-block-list\"><li>Setup will remind you to remove Microsoft Endpoint Protection:\n\n<\/li><\/ol>\n\n\n\n<ol class=\"wp-block-list\"><li>To remove Microsoft Endpoint Protection: Open the Control Panel | Programs and Features, and Uninstall using the\nright-mouse menu option:\n\n<\/li><\/ol>\n\n\n\n<ol class=\"wp-block-list\"><li>When the analysis phase is complete, setup will prompt you to \npress Back to change choices, or to proceed with the In-place Upgrade, \npress <strong>Install<\/strong>:\n\n<\/li><\/ol>\n\n\n\n<ol class=\"wp-block-list\"><li>On the Ready to install screen, click Install to start the installation.\n\n<\/li><\/ol>\n\n\n\n<ol class=\"wp-block-list\"><li>Setup will proceed with the In-place Upgrade, and then the server will reboot:\n\n<\/li><\/ol>\n\n\n\n<ol class=\"wp-block-list\"><li>Setup will complete and the server will reboot.<\/li><\/ol>\n\n\n\n<h2 class=\"wp-block-heading\">Post Upgrade: Windows Server 2016<\/h2>\n\n\n\n<hr class=\"wp-block-separator\"\/>\n\n\n\n<ol class=\"wp-block-list\"><li>After Setup has completed installing and rebooted the sever, \nlogin to check that the server has been successfully upgraded. If you \nselected Windows Server 2016 Standard or Datacenter Desktop Edition, you\n should see the Server Manager window:\n\n<\/li><\/ol>\n\n\n\n<ol class=\"wp-block-list\"><li>Run <strong>RegEdit<\/strong> and check the value of the <strong>HKEY_LOCAL_MACHINE\\SOFTWARE\\Microsoft\\WindowsNT\\CurrentVersion<\/strong> hive \u2013 the version should be successfully updated to Windows Server 2016.\n\n<\/li><\/ol>\n\n\n\n<ol class=\"wp-block-list\"><li>Check that applications are running and that client connections to the applications succeed.\n<\/li><li>If you believe that there has been an issue upgrading your server, you should copy and Zip the <strong>%SystemRoot%\\Panther<\/strong> (usually <strong>C:\\Windows\\Panther<\/strong>) directory and contact support.\n<\/li><\/ol>\n\n\n\n<h2 class=\"wp-block-heading\">Upgrade 3 of 3: Windows Server 2016 to Windows Server 2019<\/h2>\n\n\n\n<hr class=\"wp-block-separator\"\/>\n\n\n\n<ol class=\"wp-block-list\"><li>Patch the server. It is strongly recommended that the server is \nfully patched, even if your previous Windows Server 2012 was fully \npatched.\n<\/li><li>Backup the Operating System, Applications, and Virtual Machines.\n<\/li><li>Locate the setup media for Windows Server 2019\n<\/li><li>Run <strong>setup.exe<\/strong> by double-clicking it:\n\n<\/li><\/ol>\n\n\n\n<ol class=\"wp-block-list\"><li>Click <strong>Yes<\/strong> to enable setup to proceed:\n\n<\/li><\/ol>\n\n\n\n<ol class=\"wp-block-list\"><li>For internet-connected devices, we recommend the <strong>Download updates, drivers and optional features option<\/strong>. Click <strong>Next<\/strong>:\n\n<\/li><\/ol>\n\n\n\n<ol class=\"wp-block-list\"><li>Setup will check the configuration of your computer \u2013 please wait:\n\n<\/li><\/ol>\n\n\n\n<ol class=\"wp-block-list\"><li>Depending on the distribution channel that you received Windows \nServer media from (Retail, Volume License, OEM, ODM, etc.) and the \nlicense for the server, you may be prompted to enter a licensing key to \nproceed.\n<\/li><li>You will be prompted to select the image of the Edition to upgrade to. Then click <strong>Next<\/strong>:\n\n<\/li><\/ol>\n\n\n\n<ol class=\"wp-block-list\"><li>Depending on the distribution channel that you received Windows \nServer media from (Retail, Volume License, OEM, ODM, etc.) you may be \npresented with different license agreements. Click <strong>Accept<\/strong>:\n\n<\/li><\/ol>\n\n\n\n<ol class=\"wp-block-list\"><li>For In-place Upgrade, select &#8220;<strong>Keep personal files and apps<\/strong>&#8221; and then click <strong>Next<\/strong>:\n\n<\/li><\/ol>\n\n\n\n<ol class=\"wp-block-list\"><li>When the analysis phase is complete, setup will prompt you to \nclick Back to change choices, or to proceed with the In-place Upgrade.  \nClick <strong>Install<\/strong>:\n\n<\/li><\/ol>\n\n\n\n<ol class=\"wp-block-list\"><li>Setup will proceed with the In-place Upgrade, and then the server will reboot:\n\n<\/li><\/ol>\n\n\n\n<ol class=\"wp-block-list\"><li>Setup will complete and the server will reboot.<\/li><\/ol>\n","protected":false},"excerpt":{"rendered":"<p>Pre-Upgrade Upgrade path: Windows Server 2008 R2 can be upgraded to Windows Server 2019 in three consecutive upgrade processes &#8211; first by upgrading to Windows Server 2012, and then upgrading Windows Server 2012 to Windows Server 2016, and then upgrading from Windows Server 2016 to Windows Server 2019. Support: In-place Upgrade is supported for Windows &hellip; <a href=\"https:\/\/greg.klonis.gr\/index.php\/upgrade-to-windows-server-2019\" class=\"more-link\">Continue reading<span class=\"screen-reader-text\"> &#8220;Upgrade to Windows Server 2019&#8221;<\/span><\/a><\/p>\n","protected":false},"author":1,"featured_media":0,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"footnotes":""},"categories":[2,47,4],"tags":[28],"class_list":["post-121","post","type-post","status-publish","format-standard","hentry","category-hyper-v","category-virtualization","category-windows-server","tag-windows-server"],"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v25.1 - https:\/\/yoast.com\/wordpress\/plugins\/seo\/ -->\n<title>Upgrade to Windows Server 2019 &#8226; Gregory Klonis IT Blog<\/title>\n<meta name=\"robots\" content=\"index, follow, max-snippet:-1, max-image-preview:large, max-video-preview:-1\" \/>\n<link rel=\"canonical\" href=\"https:\/\/greg.klonis.gr\/index.php\/upgrade-to-windows-server-2019\" \/>\n<meta property=\"og:locale\" content=\"en_US\" \/>\n<meta property=\"og:type\" content=\"article\" \/>\n<meta property=\"og:title\" content=\"Upgrade to Windows Server 2019 &#8226; Gregory Klonis IT Blog\" \/>\n<meta property=\"og:description\" content=\"Pre-Upgrade Upgrade path: Windows Server 2008 R2 can be upgraded to Windows Server 2019 in three consecutive upgrade processes &#8211; first by upgrading to Windows Server 2012, and then upgrading Windows Server 2012 to Windows Server 2016, and then upgrading from Windows Server 2016 to Windows Server 2019. 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