When debugging an assembly loaded using the AppDomain. The assembly is loaded using the Load(byte[] rawAssembly, byte[] rawSymbolStore) method similar to the one on the Assembly class. The debugger refuses to step through to the code found in an external assembly and all attempts to step into will fail.
This can be easily reproduced using this publicly available repository: PluginTest.
To test the issue run the Server Application. You will be presented with the following page:

The Load 'InnerPlugin' Plugin button provides an in assembly variation of a Plugin which can debugged inside the Index.razor - See the LoadInnerPlugin method.
The Load 'StandalonePlugin' Plugin however exposes the debugging issue, where the assembly is loaded from an array of bytes, with the PDB supplied as well. Attempting to step into the plugin.Initialise(); expression will show the issue - Inside the LoadStandalonePlugin method in the same Index.razor.
No exceptions are raised inside visual studio or the browser.
.NET SDK (reflecting any global.json):
Version: 5.0.100-preview.6.20318.15
Commit: 4356580024
Runtime Environment:
OS Name: Windows
OS Version: 10.0.18363
OS Platform: Windows
RID: win10-x64
Base Path: C:\Program Files\dotnet\sdk\5.0.100-preview.6.20318.15\
Host (useful for support):
Version: 5.0.0-preview.6.20305.6
Commit: 4ba9ecaabd
.NET SDKs installed:
2.2.301 [C:\Program Files\dotnet\sdk]
3.1.100 [C:\Program Files\dotnet\sdk]
3.1.201 [C:\Program Files\dotnet\sdk]
3.1.300 [C:\Program Files\dotnet\sdk]
3.1.400-preview-015178 [C:\Program Files\dotnet\sdk]
5.0.100-preview.6.20318.15 [C:\Program Files\dotnet\sdk]
.NET runtimes installed:
Microsoft.AspNetCore.All 2.1.16 [C:\Program Files\dotnet\shared\Microsoft.AspNetCore.All]
Microsoft.AspNetCore.All 2.1.18 [C:\Program Files\dotnet\shared\Microsoft.AspNetCore.All]
Microsoft.AspNetCore.All 2.2.6 [C:\Program Files\dotnet\shared\Microsoft.AspNetCore.All]
Microsoft.AspNetCore.All 2.2.8 [C:\Program Files\dotnet\shared\Microsoft.AspNetCore.All]
Microsoft.AspNetCore.App 2.1.16 [C:\Program Files\dotnet\shared\Microsoft.AspNetCore.App]
Microsoft.AspNetCore.App 2.1.18 [C:\Program Files\dotnet\shared\Microsoft.AspNetCore.App]
Microsoft.AspNetCore.App 2.2.6 [C:\Program Files\dotnet\shared\Microsoft.AspNetCore.App]
Microsoft.AspNetCore.App 2.2.8 [C:\Program Files\dotnet\shared\Microsoft.AspNetCore.App]
Microsoft.AspNetCore.App 3.0.3 [C:\Program Files\dotnet\shared\Microsoft.AspNetCore.App]
Microsoft.AspNetCore.App 3.1.0 [C:\Program Files\dotnet\shared\Microsoft.AspNetCore.App]
Microsoft.AspNetCore.App 3.1.2 [C:\Program Files\dotnet\shared\Microsoft.AspNetCore.App]
Microsoft.AspNetCore.App 3.1.3 [C:\Program Files\dotnet\shared\Microsoft.AspNetCore.App]
Microsoft.AspNetCore.App 3.1.4 [C:\Program Files\dotnet\shared\Microsoft.AspNetCore.App]
Microsoft.AspNetCore.App 5.0.0-preview.6.20312.15 [C:\Program Files\dotnet\shared\Microsoft.AspNetCore.App]
Microsoft.NETCore.App 2.1.16 [C:\Program Files\dotnet\shared\Microsoft.NETCore.App]
Microsoft.NETCore.App 2.1.18 [C:\Program Files\dotnet\shared\Microsoft.NETCore.App]
Microsoft.NETCore.App 2.2.6 [C:\Program Files\dotnet\shared\Microsoft.NETCore.App]
Microsoft.NETCore.App 2.2.8 [C:\Program Files\dotnet\shared\Microsoft.NETCore.App]
Microsoft.NETCore.App 3.0.3 [C:\Program Files\dotnet\shared\Microsoft.NETCore.App]
Microsoft.NETCore.App 3.1.0 [C:\Program Files\dotnet\shared\Microsoft.NETCore.App]
Microsoft.NETCore.App 3.1.2 [C:\Program Files\dotnet\shared\Microsoft.NETCore.App]
Microsoft.NETCore.App 3.1.3 [C:\Program Files\dotnet\shared\Microsoft.NETCore.App]
Microsoft.NETCore.App 3.1.4 [C:\Program Files\dotnet\shared\Microsoft.NETCore.App]
Microsoft.NETCore.App 5.0.0-preview.6.20305.6 [C:\Program Files\dotnet\shared\Microsoft.NETCore.App]
Microsoft.WindowsDesktop.App 3.0.3 [C:\Program Files\dotnet\shared\Microsoft.WindowsDesktop.App]
Microsoft.WindowsDesktop.App 3.1.0 [C:\Program Files\dotnet\shared\Microsoft.WindowsDesktop.App]
Microsoft.WindowsDesktop.App 3.1.2 [C:\Program Files\dotnet\shared\Microsoft.WindowsDesktop.App]
Microsoft.WindowsDesktop.App 3.1.3 [C:\Program Files\dotnet\shared\Microsoft.WindowsDesktop.App]
Microsoft.WindowsDesktop.App 3.1.4 [C:\Program Files\dotnet\shared\Microsoft.WindowsDesktop.App]
Microsoft.WindowsDesktop.App 5.0.0-preview.6.20308.1 [C:\Program Files\dotnet\shared\Microsoft.WindowsDesktop.App]
Another similar issue with this style of assembly loading: https://github.com/enkodellc/blazorboilerplate/issues/264
Thanks for contacting us.
We're moving this issue to the Next sprint planning milestone for future evaluation / consideration. We will evaluate the request when we are planning the work for the next milestone. To learn more about what to expect next and how this issue will be handled you can read more about our triage process here.
@mkArtakMSFT I think we should track this for rc1 as a tooling follow-up to the lazy-load work.
Let's see if we can find a cheap solution for this in RC1.
@lewing This is the issue that we can use to brainstorm solutions to the problem of adding debugging support for assemblies that are lazily-loaded after the application (and debugging proxy) has been launched.
Thanks for contacting us.
We're moving this issue to the Next sprint planning milestone for future evaluation / consideration. We will evaluate the request when we are planning the work for the next milestone. To learn more about what to expect next and how this issue will be handled you can read more about our triage process here.