diff --git a/eng/DependencyManagement.psm1 b/eng/DependencyManagement.psm1
index ca2f65aa5a..21c3899ce9 100644
--- a/eng/DependencyManagement.psm1
+++ b/eng/DependencyManagement.psm1
@@ -33,3 +33,7 @@ function Get-ProductReleaseState() {
         return 'Prerelease'
     }
 }
+
+function Get-DockerOs() {
+    return docker version -f "{{ .Server.Os }}"
+}
diff --git a/eng/dockerfile-templates/Get-GeneratedDockerfiles.ps1 b/eng/dockerfile-templates/Get-GeneratedDockerfiles.ps1
index dcd79a1ed9..fff42ae0ab 100644
--- a/eng/dockerfile-templates/Get-GeneratedDockerfiles.ps1
+++ b/eng/dockerfile-templates/Get-GeneratedDockerfiles.ps1
@@ -24,7 +24,9 @@ if (-Not $OutputDirectory) {
 $onDockerfilesGenerated = {
     param($ContainerName)
 
-    if (-Not $Validate) {
+    # On Windows, ImageBuilder is run locally due to limitations with running Docker client within a container.
+    # Remove linux condition when https://github.com/dotnet/docker-tools/issues/159 is resolved
+    if ($(Get-DockerOs) -eq "linux" -and -not $Validate) {
         Exec "docker cp ${ContainerName}:/repo/src $OutputDirectory"
     }
 }
diff --git a/eng/readme-templates/Get-GeneratedReadmes.ps1 b/eng/readme-templates/Get-GeneratedReadmes.ps1
index b0d3c53f70..cafcb7bf20 100644
--- a/eng/readme-templates/Get-GeneratedReadmes.ps1
+++ b/eng/readme-templates/Get-GeneratedReadmes.ps1
@@ -21,7 +21,9 @@ function CopyReadme([string]$containerName, [string]$readmeRelativePath) {
 $onDockerfilesGenerated = {
     param($ContainerName)
 
-    if (-Not $Validate) {
+    # On Windows, ImageBuilder is run locally due to limitations with running Docker client within a container.
+    # Remove linux condition when https://github.com/dotnet/docker-tools/issues/159 is resolved.
+    if ($(Get-DockerOs) -eq "linux" -and -not $Validate) {
         CopyReadme $ContainerName "README.aspire-dashboard.md"
         CopyReadme $ContainerName "README.aspnet.md"
         CopyReadme $ContainerName "README.md"