New Client - Windows 10 Upgrade Path



  • I picked up a new client and reviewed their current network and PC state. I'm looking for the most effective upgrade path to Windows 10 and hoping I can get a few suggestions. Here is what they have...

    • There are a total of 8 PCs, all Windows (Windows is required as their property management software only runs on Windows)
    • All PCs are running various versions of Windows 7 Home Premium and Windows 7 Pro
    • There are 5 different types of PC configs each with its own set of installed applications (and just to add to the fun, they haven't been able to locate the install media for all of those applications)
    • PCs are between 3-4 yrs old (and no plans on hardware upgrades for a coulpe years) and not all same brand/model
    • All PCs running Office 2016 (installed from their Office 365 Business Premium license)
    • All Windows licenses installed on PCs at time of purchase (no licensed image rights for Windows)
    • No DC, only running in Workgroup
    • No onsite or cloud servers, only a Synology NAS for file sharing and a remote Synology NAS for backup
    • All users were running as admin (that was the first fix implemented)
    • I'm likely going to setup JumpCloud for identity management

    Am I wrong in thinking that if they want to stick with current hardware, an in-place upgrade is the most likely best option? My experience with in-place upgrades is that there's always something that gets FUBAR so not really a fan of this. Any other recommended approach? I realize it would be simpler to get hardware upgraded and proper Windows image rights and it is certainly an option I'll present but need to provide the cost alternatives for the upgrade path. In my mind, hardware + Windows image rights + Windows licenses = less costly option rather than my team doing in-place upgrades.



  • @nashbrydges said in New Client - Windows 10 Upgrade Path:

    I'm likely going to setup JumpCloud for identity management

    Any particular reason this is necessary? Are they going to be moving between computers? Seems like this isn't that big a deal if there are only 8 computers and no one will be sharing.



  • @nashbrydges said in New Client - Windows 10 Upgrade Path:

    In my mind, hardware + Windows image rights + Windows licenses = less costly option rather than my team doing in-place upgrades.

    Is this true? Seems like it it would be more costly to setup a standard image and then go to each computer to deploy it. It might not be but it could be.

    Any reason they need to be upgraded to Windows 10 now? Windows 7 is still supported and getting software and security updates. Why not upgrade them to the newest version when their hardware starts to die or they deem a replacement is necessary?



  • @nashbrydges said in New Client - Windows 10 Upgrade Path:

    No onsite or cloud servers, only a Synology NAS for file sharing and a remote Synology NAS for backup

    For the size of the business this probably isn't a bad thing, how much data do they have? No need for an on-site server if they don't have a business need for one.



  • @nashbrydges assuming they no longer have access to the free upgrade, I would simply purchase 8 copies of Windows 10 Pro, and do inline upgrades of each system.

    Of course since you have the challenge of no installation media for the required software you need to have a backup process first.

    Personally, you can just clone each of the disks to a larger disk that is lying around. Or backup the disk to an SMB or NFS server using something like UrBackup.

    Each has their pros and cons, but performing block level backups of these snowflake systems might be the key to keeping the customer happy.



  • Of course the next fun part would be the inability to upgrade between different versions of Windows (home, premium, pro etc) and then from Windows 7 to Windows 10.



  • @coliver said in New Client - Windows 10 Upgrade Path:

    @nashbrydges said in New Client - Windows 10 Upgrade Path:

    I'm likely going to setup JumpCloud for identity management

    Any particular reason this is necessary? Are they going to be moving between computers? Seems like this isn't that big a deal if there are only 8 computers and no one will be sharing.

    They have 2 offices and some staff move between them.



  • I would push them to purchase Win 10 Pro and an SSD for each machine. I fight people all the time trying to convince them to do an SSD swap. After they see the difference in performance, they regret not doing it sooner.



  • @coliver said in New Client - Windows 10 Upgrade Path:

    @nashbrydges said in New Client - Windows 10 Upgrade Path:

    In my mind, hardware + Windows image rights + Windows licenses = less costly option rather than my team doing in-place upgrades.

    Is this true? Seems like it it would be more costly to setup a standard image and then go to each computer to deploy it. It might not be but it could be.

    Any reason they need to be upgraded to Windows 10 now? Windows 7 is still supported and getting software and security updates. Why not upgrade them to the newest version when their hardware starts to die or they deem a replacement is necessary?

    One of their applications is not supported on Windows 7 Home and they've had issues that the software vendor won't support because of the Win version. The software vendor is also discontinuing support for Win 7 altogether in Oct 2018. Makes less sense (to me anyway) to upgrade 5 PCs to Win 7 Pro only to do this again in the near future to Win 10. Having a single Windows version also makes management/support easier.



  • @coliver said in New Client - Windows 10 Upgrade Path:

    @nashbrydges said in New Client - Windows 10 Upgrade Path:

    No onsite or cloud servers, only a Synology NAS for file sharing and a remote Synology NAS for backup

    For the size of the business this probably isn't a bad thing, how much data do they have? No need for an on-site server if they don't have a business need for one.

    Exactly. Not planning on changing this. They have a working setup that fits their needs.



  • @nashbrydges said in New Client - Windows 10 Upgrade Path:

    • There are 5 different types of PC configs each with its own set of installed applications (and just to add to the fun, they haven't been able to locate the install media for all of those applications)

    You may want to download and run the compatibility tool first. Some of the installed apps without media may be incompatible.

    I've run into a few apps that were removed after a Win10 upgrade.



  • @nashbrydges said in New Client - Windows 10 Upgrade Path:

    @coliver said in New Client - Windows 10 Upgrade Path:

    @nashbrydges said in New Client - Windows 10 Upgrade Path:

    In my mind, hardware + Windows image rights + Windows licenses = less costly option rather than my team doing in-place upgrades.

    Is this true? Seems like it it would be more costly to setup a standard image and then go to each computer to deploy it. It might not be but it could be.

    Any reason they need to be upgraded to Windows 10 now? Windows 7 is still supported and getting software and security updates. Why not upgrade them to the newest version when their hardware starts to die or they deem a replacement is necessary?

    One of their applications is not supported on Windows 7 Home and they've had issues that the software vendor won't support because of the Win version. The software vendor is also discontinuing support for Win 7 altogether in Oct 2018. Makes less sense (to me anyway) to upgrade 5 PCs to Win 7 Pro only to do this again in the near future to Win 10. Having a single Windows version also makes management/support easier.

    Then I would say move the 5 PCs that are on Windows 7 Home to Windows 10, you'll have to get the Pro license anyway and you should be able to do an in-place upgrade.

    https://docs.microsoft.com/en-us/windows/deployment/upgrade/windows-10-upgrade-paths



  • @pmoncho Good point. I'll add that to my task list.



  • @nashbrydges said in New Client - Windows 10 Upgrade Path:

    I picked up a new client and reviewed their current network and PC state. I'm looking for the most effective upgrade path to Windows 10 and hoping I can get a few suggestions. Here is what they have...

    • There are a total of 8 PCs, all Windows (Windows is required as their property management software only runs on Windows)
    • All PCs are running various versions of Windows 7 Home Premium and Windows 7 Pro
    • There are 5 different types of PC configs each with its own set of installed applications (and just to add to the fun, they haven't been able to locate the install media for all of those applications)
    • PCs are between 3-4 yrs old (and no plans on hardware upgrades for a coulpe years) and not all same brand/model
    • All PCs running Office 2016 (installed from their Office 365 Business Premium license)
    • All Windows licenses installed on PCs at time of purchase (no licensed image rights for Windows)
    • No DC, only running in Workgroup
    • No onsite or cloud servers, only a Synology NAS for file sharing and a remote Synology NAS for backup
    • All users were running as admin (that was the first fix implemented)
    • I'm likely going to setup JumpCloud for identity management

    Am I wrong in thinking that if they want to stick with current hardware, an in-place upgrade is the most likely best option? My experience with in-place upgrades is that there's always something that gets FUBAR so not really a fan of this. Any other recommended approach? I realize it would be simpler to get hardware upgraded and proper Windows image rights and it is certainly an option I'll present but need to provide the cost alternatives for the upgrade path. In my mind, hardware + Windows image rights + Windows licenses = less costly option rather than my team doing in-place upgrades.

    Jumpcloud with less than 10 users is free so that is a great thing. Now for the upgrade, you can buy the Windows 10 Pro and then upgrade the WIndows 7 Home Premium and Pro machines to Windows 10 Pro as below:
    https://www.microsoft.com/en-us/store/d/windows-10-pro/df77x4d43rkt/48DN?SilentAuth=1&wa=wsignin1.0
    0_1517925381840_2018-02-06_0856.png



  • @coliver said in New Client - Windows 10 Upgrade Path:

    @nashbrydges said in New Client - Windows 10 Upgrade Path:

    @coliver said in New Client - Windows 10 Upgrade Path:

    @nashbrydges said in New Client - Windows 10 Upgrade Path:

    In my mind, hardware + Windows image rights + Windows licenses = less costly option rather than my team doing in-place upgrades.

    Is this true? Seems like it it would be more costly to setup a standard image and then go to each computer to deploy it. It might not be but it could be.

    Any reason they need to be upgraded to Windows 10 now? Windows 7 is still supported and getting software and security updates. Why not upgrade them to the newest version when their hardware starts to die or they deem a replacement is necessary?

    One of their applications is not supported on Windows 7 Home and they've had issues that the software vendor won't support because of the Win version. The software vendor is also discontinuing support for Win 7 altogether in Oct 2018. Makes less sense (to me anyway) to upgrade 5 PCs to Win 7 Pro only to do this again in the near future to Win 10. Having a single Windows version also makes management/support easier.

    Then I would say move the 5 PCs that are on Windows 7 Home to Windows 10, you'll have to get the Pro license anyway and you should be able to do an in-place upgrade.

    https://docs.microsoft.com/en-us/windows/deployment/upgrade/windows-10-upgrade-paths

    You beat me to it 🙂



  • @dbeato said in New Client - Windows 10 Upgrade Path:

    @nashbrydges said in New Client - Windows 10 Upgrade Path:

    I picked up a new client and reviewed their current network and PC state. I'm looking for the most effective upgrade path to Windows 10 and hoping I can get a few suggestions. Here is what they have...

    • There are a total of 8 PCs, all Windows (Windows is required as their property management software only runs on Windows)
    • All PCs are running various versions of Windows 7 Home Premium and Windows 7 Pro
    • There are 5 different types of PC configs each with its own set of installed applications (and just to add to the fun, they haven't been able to locate the install media for all of those applications)
    • PCs are between 3-4 yrs old (and no plans on hardware upgrades for a coulpe years) and not all same brand/model
    • All PCs running Office 2016 (installed from their Office 365 Business Premium license)
    • All Windows licenses installed on PCs at time of purchase (no licensed image rights for Windows)
    • No DC, only running in Workgroup
    • No onsite or cloud servers, only a Synology NAS for file sharing and a remote Synology NAS for backup
    • All users were running as admin (that was the first fix implemented)
    • I'm likely going to setup JumpCloud for identity management

    Am I wrong in thinking that if they want to stick with current hardware, an in-place upgrade is the most likely best option? My experience with in-place upgrades is that there's always something that gets FUBAR so not really a fan of this. Any other recommended approach? I realize it would be simpler to get hardware upgraded and proper Windows image rights and it is certainly an option I'll present but need to provide the cost alternatives for the upgrade path. In my mind, hardware + Windows image rights + Windows licenses = less costly option rather than my team doing in-place upgrades.

    Jumpcloud with less than 10 users is free so that is a great thing. Now for the upgrade, you can buy the Windows 10 Pro and then upgrade the WIndows 7 Home Premium and Pro machines to Windows 10 Pro as below:
    https://www.microsoft.com/en-us/store/d/windows-10-pro/df77x4d43rkt/48DN?SilentAuth=1&wa=wsignin1.0
    0_1517925381840_2018-02-06_0856.png

    That's something to check. How many users do you have?



  • @coliver said in New Client - Windows 10 Upgrade Path:

    @dbeato said in New Client - Windows 10 Upgrade Path:

    @nashbrydges said in New Client - Windows 10 Upgrade Path:

    I picked up a new client and reviewed their current network and PC state. I'm looking for the most effective upgrade path to Windows 10 and hoping I can get a few suggestions. Here is what they have...

    • There are a total of 8 PCs, all Windows (Windows is required as their property management software only runs on Windows)
    • All PCs are running various versions of Windows 7 Home Premium and Windows 7 Pro
    • There are 5 different types of PC configs each with its own set of installed applications (and just to add to the fun, they haven't been able to locate the install media for all of those applications)
    • PCs are between 3-4 yrs old (and no plans on hardware upgrades for a coulpe years) and not all same brand/model
    • All PCs running Office 2016 (installed from their Office 365 Business Premium license)
    • All Windows licenses installed on PCs at time of purchase (no licensed image rights for Windows)
    • No DC, only running in Workgroup
    • No onsite or cloud servers, only a Synology NAS for file sharing and a remote Synology NAS for backup
    • All users were running as admin (that was the first fix implemented)
    • I'm likely going to setup JumpCloud for identity management

    Am I wrong in thinking that if they want to stick with current hardware, an in-place upgrade is the most likely best option? My experience with in-place upgrades is that there's always something that gets FUBAR so not really a fan of this. Any other recommended approach? I realize it would be simpler to get hardware upgraded and proper Windows image rights and it is certainly an option I'll present but need to provide the cost alternatives for the upgrade path. In my mind, hardware + Windows image rights + Windows licenses = less costly option rather than my team doing in-place upgrades.

    Jumpcloud with less than 10 users is free so that is a great thing. Now for the upgrade, you can buy the Windows 10 Pro and then upgrade the WIndows 7 Home Premium and Pro machines to Windows 10 Pro as below:
    https://www.microsoft.com/en-us/store/d/windows-10-pro/df77x4d43rkt/48DN?SilentAuth=1&wa=wsignin1.0
    0_1517925381840_2018-02-06_0856.png

    That's something to check. How many users do you have?

    Should have mentioned this. There are 6 users total. 1 hoteling PC per location.



  • @nashbrydges said in New Client - Windows 10 Upgrade Path:

    @coliver said in New Client - Windows 10 Upgrade Path:

    @dbeato said in New Client - Windows 10 Upgrade Path:

    @nashbrydges said in New Client - Windows 10 Upgrade Path:

    I picked up a new client and reviewed their current network and PC state. I'm looking for the most effective upgrade path to Windows 10 and hoping I can get a few suggestions. Here is what they have...

    • There are a total of 8 PCs, all Windows (Windows is required as their property management software only runs on Windows)
    • All PCs are running various versions of Windows 7 Home Premium and Windows 7 Pro
    • There are 5 different types of PC configs each with its own set of installed applications (and just to add to the fun, they haven't been able to locate the install media for all of those applications)
    • PCs are between 3-4 yrs old (and no plans on hardware upgrades for a coulpe years) and not all same brand/model
    • All PCs running Office 2016 (installed from their Office 365 Business Premium license)
    • All Windows licenses installed on PCs at time of purchase (no licensed image rights for Windows)
    • No DC, only running in Workgroup
    • No onsite or cloud servers, only a Synology NAS for file sharing and a remote Synology NAS for backup
    • All users were running as admin (that was the first fix implemented)
    • I'm likely going to setup JumpCloud for identity management

    Am I wrong in thinking that if they want to stick with current hardware, an in-place upgrade is the most likely best option? My experience with in-place upgrades is that there's always something that gets FUBAR so not really a fan of this. Any other recommended approach? I realize it would be simpler to get hardware upgraded and proper Windows image rights and it is certainly an option I'll present but need to provide the cost alternatives for the upgrade path. In my mind, hardware + Windows image rights + Windows licenses = less costly option rather than my team doing in-place upgrades.

    Jumpcloud with less than 10 users is free so that is a great thing. Now for the upgrade, you can buy the Windows 10 Pro and then upgrade the WIndows 7 Home Premium and Pro machines to Windows 10 Pro as below:
    https://www.microsoft.com/en-us/store/d/windows-10-pro/df77x4d43rkt/48DN?SilentAuth=1&wa=wsignin1.0
    0_1517925381840_2018-02-06_0856.png

    That's something to check. How many users do you have?

    Should have mentioned this. There are 6 users total. 1 hoteling PC per location.

    Then Jumpcloud would work for you. Good to know.



  • For the 10 users of JumpCloud see below:
    0_1517925832719_2018-02-06_0903.png



  • @dbeato @coliver I use JumpCloud for my team so I was familiar with the free 10 users which is pretty nice for small clients.



  • @nashbrydges said in New Client - Windows 10 Upgrade Path:

    @coliver said in New Client - Windows 10 Upgrade Path:

    @nashbrydges said in New Client - Windows 10 Upgrade Path:

    I'm likely going to setup JumpCloud for identity management

    Any particular reason this is necessary? Are they going to be moving between computers? Seems like this isn't that big a deal if there are only 8 computers and no one will be sharing.

    They have 2 offices and some staff move between them.

    Remote Office,.. Any chance to push them to use TS and be 'free to do as needed' on the work stations?


  • Service Provider

    @gjacobse said in New Client - Windows 10 Upgrade Path:

    @nashbrydges said in New Client - Windows 10 Upgrade Path:

    @coliver said in New Client - Windows 10 Upgrade Path:

    @nashbrydges said in New Client - Windows 10 Upgrade Path:

    I'm likely going to setup JumpCloud for identity management

    Any particular reason this is necessary? Are they going to be moving between computers? Seems like this isn't that big a deal if there are only 8 computers and no one will be sharing.

    They have 2 offices and some staff move between them.

    Remote Office,.. Any chance to push them to use TS and be 'free to do as needed' on the work stations?

    Ewwwwwww


  • Service Provider

    @nashbrydges said in New Client - Windows 10 Upgrade Path:

    Drop Veeam Endpoint on all the desktops.
    Make a new share on the Synology (with new permissions that are only used by Veeam).

    Once you have that, then you can proceed with the upgrades.

    In place upgrades suck, but if you do not have the install media, just do it anyway. You can always install clean once you have media down the road.


  • Service Provider

    @nashbrydges said in New Client - Windows 10 Upgrade Path:

    Windows image rights and it is certainly an option I'll present but need to provide the cost alternatives for the upgrade path. In my mind, hardware + Windows image rights + Windows licenses = less costly option rather than my team doing in-place upgrades.

    This is stupid for the scale. You will spend way too much time prepping images for no reason.

    You can install a clean Win 10 almost just as fast as an image. and then you do not have the pain of MS VLSC tracking.

    Imaging is nice when it fits the problem, but not for this.


 

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