diff --git a/package.json b/package.json
index 55a542770f..6d705e137e 100644
--- a/package.json
+++ b/package.json
@@ -501,6 +501,52 @@
               "request": "attach",
               "processId": "current"
             }
+          },
+          {
+            "label": "PowerShell: Run Pester Tests",
+            "description": "Debug Pester Tests detected in your current directory (runs Invoke-Pester)",
+            "body": {
+              "name": "PowerShell Run Pester Tests",
+              "type": "PowerShell",
+              "request": "launch",
+              "script": "Invoke-Pester",
+              "createTemporaryIntegratedConsole": true,
+              "attachDotnetDebugger": true
+            }
+          },
+          {
+            "label": "PowerShell: Interactive Session (Module)",
+            "description": "Debug commands executed from the PowerShell Extension Terminal after auto-loading your module",
+            "body": {
+              "name": "PowerShell: Module Interactive Session",
+              "type": "PowerShell",
+              "request": "launch",
+              "script": "Enter command to import your binary module, for example: \"Import-Module -Force ${workspaceFolder}/path/to/module.psd1|dll\""
+            }
+          },
+          {
+            "label": "PowerShell: Interactive Session (Binary Module)",
+            "description": "Debug a .NET binary or hybrid module loaded into a PowerShell session. Breakpoints you set in your .NET (C#/F#/VB/etc.) code will be hit upon command execution. You may want to add a compile or watch action as a pre-launch task to this configuration.",
+            "body": {
+              "name": "PowerShell: Binary Module Interactive",
+              "type": "PowerShell",
+              "request": "launch",
+              "script": "Enter command to import your binary module, for example: \"Import-Module -Force ${workspaceFolder}/path/to/module.psd1|dll\"",
+              "createTemporaryIntegratedConsole": true,
+              "attachDotnetDebugger": true
+            }
+          },
+          {
+            "label": "Run Pester Tests (Binary Module)",
+            "description": "Debug a .NET binary or hybrid module by running Pester tests. Breakpoints you set in your .NET (C#/F#/VB/etc.) code will be hit upon command execution. You may want to add a compile or watch action as a pre-launch task to this configuration.",
+            "body": {
+              "name": "PowerShell: Binary Module Pester Tests",
+              "type": "PowerShell",
+              "request": "launch",
+              "script": "Invoke-Pester",
+              "createTemporaryIntegratedConsole": true,
+              "attachDotnetDebugger": true
+            }
           }
         ],
         "configurationAttributes": {
diff --git a/src/features/DebugSession.ts b/src/features/DebugSession.ts
index 792d92ebed..38d9eef462 100644
--- a/src/features/DebugSession.ts
+++ b/src/features/DebugSession.ts
@@ -21,7 +21,8 @@ import {
     CancellationTokenSource,
     InputBoxOptions,
     QuickPickItem,
-    QuickPickOptions
+    QuickPickOptions,
+    DebugConfigurationProviderTriggerKind
 } from "vscode";
 import { NotificationType, RequestType } from "vscode-languageclient";
 import { LanguageClient } from "vscode-languageclient/node";
@@ -60,6 +61,7 @@ const PREVENT_DEBUG_START = undefined;
 const PREVENT_DEBUG_START_AND_OPEN_DEBUGCONFIG = null;
 
 /** Represents the various built-in debug configurations that will be advertised to the user if they choose "Add Config" from the launch debug config window */
+// NOTE: These are duplicated with what is in package.json until https://github.com/microsoft/vscode/issues/150663#issuecomment-1506134754 is resolved.
 export const defaultDebugConfigurations: Record<DebugConfig, DebugConfiguration> = {
     [DebugConfig.LaunchCurrentFile]: {
         name: "PowerShell: Launch Current File",
@@ -129,7 +131,12 @@ export class DebugSessionFeature extends LanguageClientConsumer
     constructor(context: ExtensionContext, private sessionManager: SessionManager, private logger: ILogger) {
         super();
         // This "activates" the debug adapter for use with  You can only do this once.
-        context.subscriptions.push(debug.registerDebugConfigurationProvider("PowerShell", this));
+        [
+            DebugConfigurationProviderTriggerKind.Initial,
+            DebugConfigurationProviderTriggerKind.Dynamic
+        ].forEach(triggerKind => {
+            context.subscriptions.push(debug.registerDebugConfigurationProvider("PowerShell", this, triggerKind));
+        });
         context.subscriptions.push(debug.registerDebugAdapterDescriptorFactory("PowerShell", this));
     }
 
@@ -199,7 +206,7 @@ export class DebugSessionFeature extends LanguageClientConsumer
             {
                 id: DebugConfig.RunPester,
                 label: "Run Pester Tests (Binary Module)",
-                description: "Debug a .NET binary or hybrid module by running pester tests. Breakpoints you set in your .NET (C#/F#/VB/etc.) code will be hit upon command execution. You may want to add a compile or watch action as a pre-launch task to this configuration.",
+                description: "Debug a .NET binary or hybrid module by running Pester tests. Breakpoints you set in your .NET (C#/F#/VB/etc.) code will be hit upon command execution. You may want to add a compile or watch action as a pre-launch task to this configuration.",
             },
         ];
 
diff --git a/test/features/DebugSession.test.ts b/test/features/DebugSession.test.ts
index 191eafa336..3539598c7e 100644
--- a/test/features/DebugSession.test.ts
+++ b/test/features/DebugSession.test.ts
@@ -64,10 +64,9 @@ describe("DebugSessionFeature", () => {
             });
 
             createDebugSessionFeatureStub({context: context});
-
             assert.ok(registerFactoryStub.calledOnce, "Debug adapter factory method called");
-            assert.ok(registerProviderStub.calledOnce, "Debug config provider method called");
-            assert.equal(context.subscriptions.length, 2, "DebugSessionFeature disposables populated");
+            assert.ok(registerProviderStub.calledTwice, "Debug config provider registered for both Initial and Dynamic");
+            assert.equal(context.subscriptions.length, 3, "DebugSessionFeature disposables populated");
             // TODO: Validate the registration content, such as the language name
         });
     });