Upgrading Server 2016 to 2019

Just before the end of February, my workstation's RAID 10 decided that it would be fun if I lost 2 drives on the same mirror.  So thankfully I had my OS on an SSD which was running but I did end up losing all my data but none of it was essential and it is pretty hard to backup 8tb.

So now that I'm more/less starting from scratch I thought it would be a great time to try an in-place upgrade of server 2016 to 2019!  HOW EXCITING!  I do have some software I will running on my C: including SQL server so it will be interesting to see what still works after the upgrade.  Now that I have some new drives and I can now setup a backup solution for some of my dev work!

Following the guide from microsoft.  https://docs.microsoft.com/en-us/windows-server/upgrade/upgrade-2016-to-2019

I saved the info they requested to a network drive and a flash drive.

open the cmd prompt and cd to c:\Windows\system32, and then type systeminfo.exe.

Results from running systeminfo.exe.

Host Name:                 "MY WORKSTATION"
OS Name:                   Microsoft Windows Server 2016 Standard
OS Version:                10.0.14393 N/A Build 14393
OS Manufacturer:           Microsoft Corporation
OS Configuration:          Standalone Server
OS Build Type:             Multiprocessor Free
Registered Owner:          Windows User
Registered Organization:
Product ID:                xxxxx-xxxxx-xxxxx-xxxxx
Original Install Date:     2018-06-18, 6:36:57 AM
System Boot Time:          2020-02-26, 9:58:13 AM
System Manufacturer:       COMPUTER INC.
System Model:              WORKSTATION
System Type:               x64-based PC
Processor(s):              2 Processor(s) Installed.
                           [01]:  ~1200 Mhz
                           [02]:  ~1200 Mhz
BIOS Version:              American Megatrends Inc.
Windows Directory:         C:\Windows
System Directory:          C:\Windows\system32
Boot Device:               \Device\HarddiskVolume4
System Locale:             en-ca;English (Canada)
Input Locale:              en-us;English (United States)
Time Zone:                 (UTC-07:00) Mountain Time (US & Canada)
Total Physical Memory:     130,958 MB
Available Physical Memory: 115,100 MB
Virtual Memory: Max Size:  150,414 MB
Virtual Memory: Available: 132,449 MB
Virtual Memory: In Use:    17,965 MB
Page File Location(s):     C:\pagefile.sys
Domain:                    "MY DOMAIN"
Logon Server:              \\LoginServer
Hotfix(s):                 14 Hotfix(s) Installed.
                           [01]: KB3192137
                           [02]: KB4091664
                           [03]: KB4093137
                           [04]: KB4132216
                           [05]: KB4465659
                           [06]: KB4485447
                           [07]: KB4498947
                           [08]: KB4503537
                           [09]: KB4509091
                           [10]: KB4512574
                           [11]: KB4520724
                           [12]: KB4521858
                           [13]: KB4524244
                           [14]: KB4537764

NETWORK INFORMATION Gets listed with all details about your networks connected, such as VLAN Tags, IPs, etc

Hyper-V Requirements:      A hypervisor has been detected. Features required for Hyper-V will not be displayed.

Run and save the information from ipconfig /all

RESULTS FROM IPCONFIG

Windows IP Configuration

   Host Name . . . . . . . . . . . . : "My Workstation"
   Primary Dns Suffix  . . . . . . . :
   Node Type . . . . . . . . . . . . : Hybrid
   IP Routing Enabled. . . . . . . . : No
   WINS Proxy Enabled. . . . . . . . : No
   DNS Suffix Search List. . . . . . : Domain1
                                       Domain2

All you networking information gets listed here starting with your default NETWORK and it lists all vlan tags, mac addresses, much as you would expect from the
"ipconfig /all" command.

Record 2 registry key entries.   BuildLabEx (version) and EditionID (edition)

I did a Registry Keys Export for a Backup and a screen shot for reference

I saved the upgrade info to a text file on the flash drive along with a screen shot of the registry and an export of the current version key.

I create upgrade media using rufus, then ran the installer as an administrator

NOTE:  You will need your server key when you upgrade

First it will check for updates, if there are none it will move on

then it will check and see if your ready to install, checking for enough disk space etc.  Here is where you will be asked for your product key

Then you will need to select your version of server in this case I'm picking (Desktop Experience)

Accept the notices and license terms

You will be asked what you want to keep, I'm going to just keep everything as is since I need to redo everything anyway.

Then it will do a check to see if there is any kind of issue in the way of the upgrade.

 Then it will ask you to install windows

I started this process at 2:30 pm and to get to 75% took about an hour and a half so it really does take it's sweet time.  So I would plan for a minimum outage of about 3 hours.  The system seemed to have taken the upgrade just fine however I was unable to connect to the server using RDP and I lost access to some unauthenticated network shares. Though I really should setup some security on this network share it is something I am not able to arbitrarily do at the moment as others require access to this share. 

So to fix this problem; you need to edit a registry entry "AllowInsecureGuestAuth"

located here (you can copy and paste the path into regedit):

Computer\HKEY_LOCAL_MACHINE\SYSTEM\CurrentControlSet\Services\LanmanWorkstation\Parameters

The update change the REG_DWORD to 0

AllowInsecureGuestAuth Value after upgrade

You need to change the value to 1 if you want to be able to access unauthenticated shares.

Change the REG_DWORD to 1 to allow access to unauthenticated shares

you can read the reference link below with the details.

https://support.microsoft.com/en-ca/help/4046019/guest-access-in-smb2-disabled-by-default-in-windows-10-and-windows-ser

Microsoft is defaulting on the side of security which I completely applaud them for; however I do have to re-enable unauthenticated access.  

It was also shortly after fixing my network share issue I noticed some issues with most of my virtual networks with most of my networks showing an error.

Most networks no longer work after upgrade.

After trying serveral times to fix the issue with updating drivers, rebooting, system scans, etc I gave up and decided that my in-place upgrade wasn't an in-place upgrade.  So I formatted my OS drive and did a clean install.

After doing a clean install of Server 2019, setting up the dual port nic into a teamed interface I still lost network connectivity after installing the Hyper-V roll.  This happened after I reinstalled another 2 times.  What I didn't realize even looking though forums this issue was hard to find a resolution to.  The only solution that worked for me was to follow this process I found on Microsoft Technet

https://social.technet.microsoft.com/Forums/en-US/5906152c-1f22-449a-b223-15c4a3e5eb36/2019-hyperv-virtual-switch-error?forum=winserverhyperv

1. I had to remove Hyper-V role
2. Restart
3. Run  netcfg -d in a privileged powershell console
4. I made sure I setup all my teamed networks after this
5. Restart 
6. Install Hyper-v role

This was what fixed my network issue in server 2019.  After running the netcfg -d command, and re-installing the hyper-v roll my virtual switches came back without an issue.  This network issue after installing the Hyper-V roll also occurred when I had set up the server on a regular network interface (NOT TEAMED).  This would not be good if I had to keep the virtual machines running but at least I would be able to export them and re-import them.  This is compelling me to try and do a mockup in place upgrade; even though this one went sideways I think I can come up with a process to do it.