diff --git a/configs/windows/MinimalAgent/nanoserver/NanoServer1809.Dockerfile b/configs/windows/MinimalAgent/nanoserver/NanoServer1809.Dockerfile
index 55ff5055..5c916c65 100644
--- a/configs/windows/MinimalAgent/nanoserver/NanoServer1809.Dockerfile
+++ b/configs/windows/MinimalAgent/nanoserver/NanoServer1809.Dockerfile
@@ -29,6 +29,10 @@ USER ContainerAdministrator
 RUN mkdir C:\\BuildAgent
 COPY TeamCity/buildAgent C:/BuildAgent
 
+# Workaround for TW-87124 - Windows-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 scripts/*.cs /scripts/
 SHELL ["pwsh", "-Command", "$ErrorActionPreference = 'Stop'; $ProgressPreference = 'SilentlyContinue';"]
 
diff --git a/context/generated/windows/MinimalAgent/nanoserver/1809/Dockerfile b/context/generated/windows/MinimalAgent/nanoserver/1809/Dockerfile
index 761862ea..f01f44db 100644
--- a/context/generated/windows/MinimalAgent/nanoserver/1809/Dockerfile
+++ b/context/generated/windows/MinimalAgent/nanoserver/1809/Dockerfile
@@ -23,6 +23,10 @@ USER ContainerAdministrator
 RUN mkdir C:\\BuildAgent
 COPY TeamCity/buildAgent C:/BuildAgent
 
+# Workaround for TW-87124 - Windows-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 scripts/*.cs /scripts/
 SHELL ["pwsh", "-Command", "$ErrorActionPreference = 'Stop'; $ProgressPreference = 'SilentlyContinue';"]
 
diff --git a/context/generated/windows/MinimalAgent/nanoserver/1903/Dockerfile b/context/generated/windows/MinimalAgent/nanoserver/1903/Dockerfile
index 824eced8..acdfdc65 100644
--- a/context/generated/windows/MinimalAgent/nanoserver/1903/Dockerfile
+++ b/context/generated/windows/MinimalAgent/nanoserver/1903/Dockerfile
@@ -23,6 +23,10 @@ USER ContainerAdministrator
 RUN mkdir C:\\BuildAgent
 COPY TeamCity/buildAgent C:/BuildAgent
 
+# Workaround for TW-87124 - Windows-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 scripts/*.cs /scripts/
 SHELL ["pwsh", "-Command", "$ErrorActionPreference = 'Stop'; $ProgressPreference = 'SilentlyContinue';"]
 
diff --git a/context/generated/windows/MinimalAgent/nanoserver/1909/Dockerfile b/context/generated/windows/MinimalAgent/nanoserver/1909/Dockerfile
index bdc0fbca..5e35b6bc 100644
--- a/context/generated/windows/MinimalAgent/nanoserver/1909/Dockerfile
+++ b/context/generated/windows/MinimalAgent/nanoserver/1909/Dockerfile
@@ -23,6 +23,10 @@ USER ContainerAdministrator
 RUN mkdir C:\\BuildAgent
 COPY TeamCity/buildAgent C:/BuildAgent
 
+# Workaround for TW-87124 - Windows-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 scripts/*.cs /scripts/
 SHELL ["pwsh", "-Command", "$ErrorActionPreference = 'Stop'; $ProgressPreference = 'SilentlyContinue';"]