diff --git a/eng/common/testproxy/docker-start-proxy.ps1 b/eng/common/testproxy/docker-start-proxy.ps1
index 4137ae2aff569..577af6d24d87c 100644
--- a/eng/common/testproxy/docker-start-proxy.ps1
+++ b/eng/common/testproxy/docker-start-proxy.ps1
@@ -64,9 +64,31 @@ if ($Mode -eq "start"){
     }
     # else we need to create it
     else {
+        $attempts = 0
         Write-Host "Attempting creation of Docker host $CONTAINER_NAME"
         Write-Host "docker container create -v `"${root}:${Initial}/etc/testproxy`" $LinuxContainerArgs -p 5001:5001 -p 5000:5000 --name $CONTAINER_NAME $SelectedImage"
-        docker container create -v "${root}:${Initial}/etc/testproxy" $LinuxContainerArgs -p 5001:5001 -p 5000:5000 --name $CONTAINER_NAME $SelectedImage
+        while($attempts -lt 3){
+            docker container create -v "${root}:${Initial}/etc/testproxy" $LinuxContainerArgs -p 5001:5001 -p 5000:5000 --name $CONTAINER_NAME $SelectedImage
+
+            if($LASTEXITCODE -ne 0){
+                $attempts += 1
+                Start-Sleep -s 10
+
+                if($attempts -lt 3){
+                    Write-Host "Attempt $attempts failed. Retrying."
+                }
+
+                continue
+            }
+            else {
+                break
+            }
+        }
+
+        if($LASTEXITCODE -ne 0){
+            Write-Host "Unable to successfully create docker container. Exiting."
+            exit(1)
+        }
     }
 
     Write-Host "Attempting start of Docker host $CONTAINER_NAME"
diff --git a/eng/common/testproxy/test-proxy-docker.yml b/eng/common/testproxy/test-proxy-docker.yml
index 97617b6fd08a7..e4e4b2c8cdb0d 100644
--- a/eng/common/testproxy/test-proxy-docker.yml
+++ b/eng/common/testproxy/test-proxy-docker.yml
@@ -6,6 +6,10 @@ steps:
         $(Build.SourcesDirectory)/eng/common/scripts/trust-proxy-certificate.ps1
     displayName: 'Language Specific Certificate Trust'
 
+  - pwsh: |
+      docker info
+    displayName: 'Dump active docker information'
+
   - pwsh: |
       $(Build.SourcesDirectory)/eng/common/testproxy/docker-start-proxy.ps1 -Mode start -TargetFolder "${{ parameters.rootFolder }}"
     displayName: 'Run the docker container'