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Background:
Several legacy Windows Server 2003 systems need to be migrated from VMware to Azure.
Yes, we know they have a legacy OS. Yet we have to keep them running. And this is (at least partly) supported by Microsoft.
One critical step is of course installing Hyper-V Integration Services on the servers before moving them to Azure. We chose to do this step manually, because the officially documented process relying on startup scripts has proven to be somewhat unreliable.
Thus, in our process, the servers will be first converted to Hyper-V machines; then HVIS will be installed and VMware Tools will be removed, and then they will be moved to Azure.

The process has been defined, tested and documented; it works correctly.

HOWEVER.

One specific system has a very weird issue with device drivers. It doesn't trust any device driver, including native ones, and asks for manual confirmation before installing any hardware. This doesn't only happen with Hyper-V drivers, but with every single device, including those whose drivers are native to Windows itself; example below:

enter image description here

This is painful (when moving from VMware to Hyper-V there are 15-20 of those prompts), but it can be survived as long as there is manual interaction with the server. However, when the server gets moved to Azure, it (presumably) waits for the same manual confirmation before installing Azure's new devices, including the new network adapter; and of course, this means no networking and no way to access the Azure VM.

Why is this happening? How can it be fixed?

We tried configuring the system to accept unsigned drivers automatically (although thay are signed and this should not happen at all):

enter image description here

However, the server still keeps doing the same and asking for confirmation before installing any new hardware (and warning that it has not passed Windows Logo testing).

We also tried sfc /scannow, which didn't detect any problem and didn't fix the issue; chkdsk also didn't find anything wrong.

Why is this specific server acting this way?
How can we fix this?

Note: this is not caused by a missing update and/or an expired certificate; I tried a new fresh install of Windows Server 2003 on Hyper-V using the original ISO (I still have a copy), so without any update at all, and it didn't do anything like this.

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  • Can you migrate to Hyper-V, click the warning messages away, and then upload it to Azure?
    – Michael Hampton
    Commented Dec 18, 2020 at 21:07
  • Yes, and that's exactly what I did. But when moving to Azure the VM gets no networking, presumably because it detects new hardware and can't install it without manual intervention (all the other 2003 servers can be moved from Hyper-V to Azure without any trouble).
    – Massimo
    Commented Dec 18, 2020 at 21:23
  • Hm, 2003 is so old it may not be able to verify the driver signatures without some sort of update (which may or may not exist) e.g. to the root certificates. Though I have no idea why ignoring doesn't seem to work.
    – Michael Hampton
    Commented Dec 18, 2020 at 21:30
  • This specific server must have something broken inside its driver management system; it doesn't recognize as valid even its own drivers (see example in the question about IDE channels).
    – Massimo
    Commented Dec 18, 2020 at 21:32
  • 1
    Oh, now I get it. You've got a proper mystery here.
    – Michael Hampton
    Commented Dec 18, 2020 at 21:47

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