diff --git a/configs/windows/MinimalAgent/nanoserver/NanoServer2022.Dockerfile b/configs/windows/MinimalAgent/nanoserver/NanoServer2022.Dockerfile
index af60e298..90b52007 100644
--- a/configs/windows/MinimalAgent/nanoserver/NanoServer2022.Dockerfile
+++ b/configs/windows/MinimalAgent/nanoserver/NanoServer2022.Dockerfile
@@ -28,12 +28,14 @@ USER ContainerAdministrator
 COPY scripts/*.cs /scripts/
 SHELL ["pwsh", "-Command", "$ErrorActionPreference = 'Stop'; $ProgressPreference = 'SilentlyContinue';"]
 
-# CaseSensitivity is essential for the agent => enforcing it. SHELL usage is mandatory (pwsh or other won't work)
-RUN mkdir C:\\BuildAgent
-SHELL ["pwsh", "-Command", "fsutil.exe", "file", "SetCaseSensitiveInfo", "C:\\BuildAgent", "enable"]
-
 # Prepare build agent distribution
+RUN mkdir C:\\BuildAgent
 COPY TeamCity/buildAgent C:/BuildAgent
+
+# Workaround for TW-87124 - Windows 2022-based plugin directories receive incorrect case, causing their inability ...
+# ... to load. The directory will be fetched from the server upon the first update with proper case.
+RUN Remove-Item -Recurse -Force C:/BuildAgent/plugins
+
 COPY run-agent.ps1 /BuildAgent/run-agent.ps1
 
 # JDK
diff --git a/context/generated/windows/MinimalAgent/nanoserver/2022/Dockerfile b/context/generated/windows/MinimalAgent/nanoserver/2022/Dockerfile
index 7e624093..4dab7a49 100644
--- a/context/generated/windows/MinimalAgent/nanoserver/2022/Dockerfile
+++ b/context/generated/windows/MinimalAgent/nanoserver/2022/Dockerfile
@@ -22,12 +22,14 @@ USER ContainerAdministrator
 COPY scripts/*.cs /scripts/
 SHELL ["pwsh", "-Command", "$ErrorActionPreference = 'Stop'; $ProgressPreference = 'SilentlyContinue';"]
 
-# CaseSensitivity is essential for the agent => enforcing it. SHELL usage is mandatory (pwsh or other won't work)
-RUN mkdir C:\\BuildAgent
-SHELL ["pwsh", "-Command", "fsutil.exe", "file", "SetCaseSensitiveInfo", "C:\\BuildAgent", "enable"]
-
 # Prepare build agent distribution
+RUN mkdir C:\\BuildAgent
 COPY TeamCity/buildAgent C:/BuildAgent
+
+# Workaround for TW-87124 - Windows 2022-based plugin directories receive incorrect case, causing their inability ...
+# ... to load. The directory will be fetched from the server upon the first update with proper case.
+RUN Remove-Item -Recurse -Force C:/BuildAgent/plugins
+
 COPY run-agent.ps1 /BuildAgent/run-agent.ps1
 
 # JDK