diff --git a/change/react-native-windows-2020-04-08-09-04-34-direct_debugging_cli.json b/change/react-native-windows-2020-04-08-09-04-34-direct_debugging_cli.json
new file mode 100644
index 00000000000..6e190fdc286
--- /dev/null
+++ b/change/react-native-windows-2020-04-08-09-04-34-direct_debugging_cli.json
@@ -0,0 +1,8 @@
+{
+  "type": "prerelease",
+  "comment": "Allow enabling of direct debugging through the CLI.",
+  "packageName": "react-native-windows",
+  "email": "12337821+nasadigital@users.noreply.github.com",
+  "dependentChangeType": "patch",
+  "date": "2020-04-08T16:04:34.634Z"
+}
\ No newline at end of file
diff --git a/vnext/Microsoft.ReactNative/ReactApplicationDelegate.cpp b/vnext/Microsoft.ReactNative/ReactApplicationDelegate.cpp
index 0dd35ba0e96..d4619d9d879 100644
--- a/vnext/Microsoft.ReactNative/ReactApplicationDelegate.cpp
+++ b/vnext/Microsoft.ReactNative/ReactApplicationDelegate.cpp
@@ -20,10 +20,27 @@ using namespace Windows::ApplicationModel::Activation;
 
 namespace winrt::Microsoft::ReactNative::implementation {
 
-static void ApplyArguments(ReactNative::ReactNativeHost const & /*host*/, std::wstring const &arguments) noexcept {
-  // Microsoft::ReactNative::implementation::ReactNativeHost* hostImpl {
-  // get_self<Microsoft::ReactNative::implementation::ReactNativeHost>(host)};
+static void ApplyArguments(ReactNative::ReactNativeHost const &host, std::wstring const &arguments) noexcept {
+  Microsoft::ReactNative::implementation::ReactNativeHost *hostImpl{
+      get_self<Microsoft::ReactNative::implementation::ReactNativeHost>(host)};
   if (!arguments.empty() /*&& host.HasInstance()*/) {
+    constexpr wchar_t delimiter = L' ';
+    std::wistringstream argumentStream(arguments);
+    std::wstring token;
+    while (std::getline(argumentStream, token, delimiter)) {
+      if (token == L"-?") {
+        std::cout << "Options:" << std::endl
+                  << "  --direct-debugging <port>    Enable direct debugging on specified port." << std::endl;
+      } else if (token == L"--direct-debugging") {
+        if (std::getline(argumentStream, token, delimiter)) {
+          const uint16_t port = static_cast<uint16_t>(std::wcstoul(token.c_str(), nullptr, 10));
+          hostImpl->InstanceSettings().UseWebDebugger(false);
+          hostImpl->InstanceSettings().UseDirectDebugger(true);
+          hostImpl->InstanceSettings().DebuggerBreakOnNextLine(true);
+          hostImpl->InstanceSettings().DebuggerPort(port);
+        }
+      }
+    }
     // TODO: check for 'remoteDebugging'.  Return if not found.  Otherwise,
     // validate a value is provided and then parse it to set the
     // ReactInstanceManager.DevSupportManager.IsRemoteDebuggingEnabled flag
diff --git a/vnext/local-cli/runWindows/runWindows.js b/vnext/local-cli/runWindows/runWindows.js
index 3a4c9e40bea..a056a7f8636 100644
--- a/vnext/local-cli/runWindows/runWindows.js
+++ b/vnext/local-cli/runWindows/runWindows.js
@@ -124,6 +124,7 @@ runWindows({
  *    no-build: Boolean - Do not build the solution
  *    no-deploy: Boolean - Do not deploy the app
  *    msBuildProps: String - Comma separated props to pass to msbuild, eg: prop1=value1,prop2=value2
+ *    direct-debugging: Number - Enable direct debugging on specified port
  */
 module.exports = {
   name: 'run-windows',
@@ -142,7 +143,7 @@ module.exports = {
     },
     {
       command: '--arch [string]',
-      description: 'The build architecture (ARM, x86, x64)',
+      description: 'The build architecture (ARM, ARM64, x86, x64)',
       default: 'x86',
     },
     {
@@ -206,5 +207,9 @@ module.exports = {
       description: 'Auto link native modules',
       default: false,
     },
+    {
+      command: '--direct-debugging [number]',
+      description: 'Enable direct debugging on specified port',
+    },
   ],
 };
diff --git a/vnext/local-cli/runWindows/utils/WindowsStoreAppUtils.ps1 b/vnext/local-cli/runWindows/utils/WindowsStoreAppUtils.ps1
index 68a76ce1874..ef23893d174 100644
--- a/vnext/local-cli/runWindows/utils/WindowsStoreAppUtils.ps1
+++ b/vnext/local-cli/runWindows/utils/WindowsStoreAppUtils.ps1
@@ -175,6 +175,6 @@ function Start-Locally {
 
     add-type -TypeDefinition $code
     $appActivator = new-object StoreAppRunner.ApplicationActivationManager
-    $args = [system.String]::Join(",", $argv)
+    $args = [system.String]::Join(" ", $argv)
     $appActivator.ActivateApplication($applicationUserModelId,$args,[StoreAppRunner.ActivateOptions]::None,[ref]0) | Out-Null
 }
diff --git a/vnext/local-cli/runWindows/utils/build.js b/vnext/local-cli/runWindows/utils/build.js
index 4d4ad38e431..e8d68401929 100644
--- a/vnext/local-cli/runWindows/utils/build.js
+++ b/vnext/local-cli/runWindows/utils/build.js
@@ -96,16 +96,15 @@ function getSolutionFile(options) {
 }
 
 function parseMsBuildProps(options) {
+  let result = {};
   if (options.msbuildprops) {
-    var result = {};
-    var props = options.msbuildprops.split(',');
-    for (var i = 0; i < props.length; i++) {
-      var prop = props[i].split('=');
+    const props = options.msbuildprops.split(',');
+    for (let i = 0; i < props.length; i++) {
+      const prop = props[i].split('=');
       result[prop[0]] = prop[1];
     }
-    return result;
   }
-  return null;
+  return result;
 }
 
 module.exports = {
diff --git a/vnext/local-cli/runWindows/utils/deploy.js b/vnext/local-cli/runWindows/utils/deploy.js
index 5bddc239f59..1225885f681 100644
--- a/vnext/local-cli/runWindows/utils/deploy.js
+++ b/vnext/local-cli/runWindows/utils/deploy.js
@@ -162,7 +162,19 @@ async function deployToDesktop(options, verbose) {
     path.join(appPackageFolder, 'Add-AppDevPackage.ps1'),
   )[0];
 
-  const args = ['remoteDebugging', options.proxy ? 'true' : 'false'];
+  let args = ['--remote-debugging', options.proxy ? 'true' : 'false'];
+
+  if (options.directDebugging) {
+    const port = parseInt(options.directDebugging, 10);
+    if (!isNaN(port) && port > 1024 && port < 65535) {
+      args.push('--direct-debugging', port.toString());
+    } else {
+      newError(
+        'Direct debugging port not specified, invalid or out of bounds.',
+      );
+      process.exit(1);
+    }
+  }
 
   const popd = pushd(options.root);