diff --git a/build.psm1 b/build.psm1
index 922cc92239..55ac81bbe7 100644
--- a/build.psm1
+++ b/build.psm1
@@ -287,10 +287,18 @@ cmd.exe /C cd /d "$location" "&" "$($vcVarsPath)\vcvarsall.bat" "$NativeHostArch
             # Copy the executable binary from the local build directory to the expected destination to enable Start-DevPowerShell to work
             #
             # TODO: This should be updated to handle per-architecture builds gracefully.
-            $srcPath = Join-Path (Join-Path (Join-Path (Get-Location) "bin") $msbuildConfiguration) "FullCLR/powershell.exe"
+
             $dstPath = ($script:Options).Top
-            log "  Copying $srcPath to $dstPath"
-            Copy-Item $srcPath $dstPath
+            @(
+                'powershell.exe',
+                'powershell.pdb',
+                'pwrshplugin.dll',
+                'pwrshplugin.pdb'
+            ) | % {
+                $srcPath = Join-Path (Join-Path (Join-Path (Get-Location) "bin") $msbuildConfiguration) "FullCLR/$_"
+                log "  Copying $srcPath to $dstPath"
+                Copy-Item $srcPath $dstPath
+            }
         } finally {
             Pop-Location
         }
diff --git a/src/Microsoft.PowerShell.ConsoleHost/project.json b/src/Microsoft.PowerShell.ConsoleHost/project.json
index a4514e0ae2..774da06990 100644
--- a/src/Microsoft.PowerShell.ConsoleHost/project.json
+++ b/src/Microsoft.PowerShell.ConsoleHost/project.json
@@ -26,6 +26,9 @@
             },
             "include" : [
                 "powershell.exe",
+                "powershell.pdb",
+                "pwrshplugin.dll",
+                "pwrshplugin.pdb",
                 "../../powershell.version"
             ]
         }
@@ -46,6 +49,9 @@
         },
         "include" : [
             "powershell.exe",
+            "powershell.pdb",
+            "pwrshplugin.dll",
+            "pwrshplugin.pdb",
             "../../powershell.version"
         ]
     },