diff --git a/package-lock.json b/package-lock.json
index 649e39db0..00c90e2ab 100644
--- a/package-lock.json
+++ b/package-lock.json
@@ -9,7 +9,7 @@
       "version": "2.34.0",
       "license": "MPL-2.0",
       "dependencies": {
-        "@vscode/extension-telemetry": "^0.4.9",
+        "@vscode/extension-telemetry": "^0.9.8",
         "@zodios/core": "^10.9.2",
         "@zodios/plugins": "^10.6.0",
         "axios": "^1.7.4",
@@ -1141,6 +1141,107 @@
         "node": ">= 12"
       }
     },
+    "node_modules/@microsoft/1ds-core-js": {
+      "version": "4.3.4",
+      "resolved": "https://registry.npmjs.org/@microsoft/1ds-core-js/-/1ds-core-js-4.3.4.tgz",
+      "integrity": "sha512-3gbDUQgAO8EoyQTNcAEkxpuPnioC0May13P1l1l0NKZ128L9Ts/sj8QsfwCRTjHz0HThlA+4FptcAJXNYUy3rg==",
+      "dependencies": {
+        "@microsoft/applicationinsights-core-js": "3.3.4",
+        "@microsoft/applicationinsights-shims": "3.0.1",
+        "@microsoft/dynamicproto-js": "^2.0.3",
+        "@nevware21/ts-async": ">= 0.5.2 < 2.x",
+        "@nevware21/ts-utils": ">= 0.11.3 < 2.x"
+      }
+    },
+    "node_modules/@microsoft/1ds-post-js": {
+      "version": "4.3.4",
+      "resolved": "https://registry.npmjs.org/@microsoft/1ds-post-js/-/1ds-post-js-4.3.4.tgz",
+      "integrity": "sha512-nlKjWricDj0Tn68Dt0P8lX9a+X7LYrqJ6/iSfQwMfDhRIGLqW+wxx8gxS+iGWC/oc8zMQAeiZaemUpCwQcwpRQ==",
+      "dependencies": {
+        "@microsoft/1ds-core-js": "4.3.4",
+        "@microsoft/applicationinsights-shims": "3.0.1",
+        "@microsoft/dynamicproto-js": "^2.0.3",
+        "@nevware21/ts-async": ">= 0.5.2 < 2.x",
+        "@nevware21/ts-utils": ">= 0.11.3 < 2.x"
+      }
+    },
+    "node_modules/@microsoft/applicationinsights-channel-js": {
+      "version": "3.3.4",
+      "resolved": "https://registry.npmjs.org/@microsoft/applicationinsights-channel-js/-/applicationinsights-channel-js-3.3.4.tgz",
+      "integrity": "sha512-Z4nrxYwGKP9iyrYtm7iPQXVOFy4FsEsX0nDKkAi96Qpgw+vEh6NH4ORxMMuES0EollBQ3faJyvYCwckuCVIj0g==",
+      "dependencies": {
+        "@microsoft/applicationinsights-common": "3.3.4",
+        "@microsoft/applicationinsights-core-js": "3.3.4",
+        "@microsoft/applicationinsights-shims": "3.0.1",
+        "@microsoft/dynamicproto-js": "^2.0.3",
+        "@nevware21/ts-async": ">= 0.5.2 < 2.x",
+        "@nevware21/ts-utils": ">= 0.11.3 < 2.x"
+      },
+      "peerDependencies": {
+        "tslib": ">= 1.0.0"
+      }
+    },
+    "node_modules/@microsoft/applicationinsights-common": {
+      "version": "3.3.4",
+      "resolved": "https://registry.npmjs.org/@microsoft/applicationinsights-common/-/applicationinsights-common-3.3.4.tgz",
+      "integrity": "sha512-4ms16MlIvcP4WiUPqopifNxcWCcrXQJ2ADAK/75uok2mNQe6ZNRsqb/P+pvhUxc8A5HRlvoXPP1ptDSN5Girgw==",
+      "dependencies": {
+        "@microsoft/applicationinsights-core-js": "3.3.4",
+        "@microsoft/applicationinsights-shims": "3.0.1",
+        "@microsoft/dynamicproto-js": "^2.0.3",
+        "@nevware21/ts-utils": ">= 0.11.3 < 2.x"
+      },
+      "peerDependencies": {
+        "tslib": ">= 1.0.0"
+      }
+    },
+    "node_modules/@microsoft/applicationinsights-core-js": {
+      "version": "3.3.4",
+      "resolved": "https://registry.npmjs.org/@microsoft/applicationinsights-core-js/-/applicationinsights-core-js-3.3.4.tgz",
+      "integrity": "sha512-MummANF0mgKIkdvVvfmHQTBliK114IZLRhTL0X0Ep+zjDwWMHqYZgew0nlFKAl6ggu42abPZFK5afpE7qjtYJA==",
+      "dependencies": {
+        "@microsoft/applicationinsights-shims": "3.0.1",
+        "@microsoft/dynamicproto-js": "^2.0.3",
+        "@nevware21/ts-async": ">= 0.5.2 < 2.x",
+        "@nevware21/ts-utils": ">= 0.11.3 < 2.x"
+      },
+      "peerDependencies": {
+        "tslib": ">= 1.0.0"
+      }
+    },
+    "node_modules/@microsoft/applicationinsights-shims": {
+      "version": "3.0.1",
+      "resolved": "https://registry.npmjs.org/@microsoft/applicationinsights-shims/-/applicationinsights-shims-3.0.1.tgz",
+      "integrity": "sha512-DKwboF47H1nb33rSUfjqI6ryX29v+2QWcTrRvcQDA32AZr5Ilkr7whOOSsD1aBzwqX0RJEIP1Z81jfE3NBm/Lg==",
+      "dependencies": {
+        "@nevware21/ts-utils": ">= 0.9.4 < 2.x"
+      }
+    },
+    "node_modules/@microsoft/applicationinsights-web-basic": {
+      "version": "3.3.4",
+      "resolved": "https://registry.npmjs.org/@microsoft/applicationinsights-web-basic/-/applicationinsights-web-basic-3.3.4.tgz",
+      "integrity": "sha512-OpEPXr8vU/t/M8T9jvWJzJx/pCyygIiR1nGM/2PTde0wn7anl71Gxl5fWol7K/WwFEORNjkL3CEyWOyDc+28AA==",
+      "dependencies": {
+        "@microsoft/applicationinsights-channel-js": "3.3.4",
+        "@microsoft/applicationinsights-common": "3.3.4",
+        "@microsoft/applicationinsights-core-js": "3.3.4",
+        "@microsoft/applicationinsights-shims": "3.0.1",
+        "@microsoft/dynamicproto-js": "^2.0.3",
+        "@nevware21/ts-async": ">= 0.5.2 < 2.x",
+        "@nevware21/ts-utils": ">= 0.11.3 < 2.x"
+      },
+      "peerDependencies": {
+        "tslib": ">= 1.0.0"
+      }
+    },
+    "node_modules/@microsoft/dynamicproto-js": {
+      "version": "2.0.3",
+      "resolved": "https://registry.npmjs.org/@microsoft/dynamicproto-js/-/dynamicproto-js-2.0.3.tgz",
+      "integrity": "sha512-JTWTU80rMy3mdxOjjpaiDQsTLZ6YSGGqsjURsY6AUQtIj0udlF/jYmhdLZu8693ZIC0T1IwYnFa0+QeiMnziBA==",
+      "dependencies": {
+        "@nevware21/ts-utils": ">= 0.10.4 < 2.x"
+      }
+    },
     "node_modules/@mswjs/cookies": {
       "version": "1.1.0",
       "resolved": "https://registry.npmjs.org/@mswjs/cookies/-/cookies-1.1.0.tgz",
@@ -1167,6 +1268,19 @@
         "node": ">=18"
       }
     },
+    "node_modules/@nevware21/ts-async": {
+      "version": "0.5.3",
+      "resolved": "https://registry.npmjs.org/@nevware21/ts-async/-/ts-async-0.5.3.tgz",
+      "integrity": "sha512-UsF7eerLsVfid7iV1oXF80qXBwHNBeqSqfh/nPZgirRU1MACmSsj83EZKS2ViFHVfSGG6WIuXMGBP6KciXfYhA==",
+      "dependencies": {
+        "@nevware21/ts-utils": ">= 0.11.5 < 2.x"
+      }
+    },
+    "node_modules/@nevware21/ts-utils": {
+      "version": "0.11.5",
+      "resolved": "https://registry.npmjs.org/@nevware21/ts-utils/-/ts-utils-0.11.5.tgz",
+      "integrity": "sha512-7nIzWKR50mf3htOg53kwPLqD5iJaRfVyBvb1NJhlIncyP1WzK8vAQbU9rqIsRtv7td1CnqspdP6IWNEjOjaeug=="
+    },
     "node_modules/@nodelib/fs.scandir": {
       "version": "2.1.5",
       "resolved": "https://registry.npmjs.org/@nodelib/fs.scandir/-/fs.scandir-2.1.5.tgz",
@@ -1690,11 +1804,16 @@
       }
     },
     "node_modules/@vscode/extension-telemetry": {
-      "version": "0.4.10",
-      "resolved": "https://registry.npmjs.org/@vscode/extension-telemetry/-/extension-telemetry-0.4.10.tgz",
-      "integrity": "sha512-XgyUoWWRQExTmd9DynIIUQo1NPex/zIeetdUAXeBjVuW9ioojM1TcDaSqOa/5QLC7lx+oEXwSU1r0XSBgzyz6w==",
+      "version": "0.9.8",
+      "resolved": "https://registry.npmjs.org/@vscode/extension-telemetry/-/extension-telemetry-0.9.8.tgz",
+      "integrity": "sha512-7YcKoUvmHlIB8QYCE4FNzt3ErHi9gQPhdCM3ZWtpw1bxPT0I+lMdx52KHlzTNoJzQ2NvMX7HyzyDwBEiMgTrWQ==",
+      "dependencies": {
+        "@microsoft/1ds-core-js": "^4.3.4",
+        "@microsoft/1ds-post-js": "^4.3.4",
+        "@microsoft/applicationinsights-web-basic": "^3.3.4"
+      },
       "engines": {
-        "vscode": "^1.60.0"
+        "vscode": "^1.75.0"
       }
     },
     "node_modules/@vscode/test-cli": {
@@ -8987,8 +9106,7 @@
     "node_modules/tslib": {
       "version": "2.6.2",
       "resolved": "https://registry.npmjs.org/tslib/-/tslib-2.6.2.tgz",
-      "integrity": "sha512-AEYxH93jGFPn/a2iVAwW87VuUIkR1FVUKB77NwMF7nBTDkDrrT/Hpt/IrCJ0QXhW27jTBDcf5ZY7w6RiqTMw2Q==",
-      "dev": true
+      "integrity": "sha512-AEYxH93jGFPn/a2iVAwW87VuUIkR1FVUKB77NwMF7nBTDkDrrT/Hpt/IrCJ0QXhW27jTBDcf5ZY7w6RiqTMw2Q=="
     },
     "node_modules/tsscmp": {
       "version": "1.0.6",
diff --git a/package.json b/package.json
index 0c1659117..876add61d 100644
--- a/package.json
+++ b/package.json
@@ -955,7 +955,7 @@
     "changelog:build": "changie batch auto && changie merge && npm i --package-lock-only"
   },
   "dependencies": {
-    "@vscode/extension-telemetry": "^0.4.9",
+    "@vscode/extension-telemetry": "^0.9.8",
     "@zodios/core": "^10.9.2",
     "@zodios/plugins": "^10.6.0",
     "axios": "^1.7.4",
diff --git a/src/extension.ts b/src/extension.ts
index ee64e53c3..167e77e3f 100644
--- a/src/extension.ts
+++ b/src/extension.ts
@@ -61,7 +61,7 @@ export async function activate(context: vscode.ExtensionContext): Promise<void>
   }
 
   const manifest = context.extension.packageJSON;
-  reporter = new TelemetryReporter(context.extension.id, manifest.version, manifest.appInsightsKey);
+  reporter = new TelemetryReporter(manifest.appInsightsKey);
   context.subscriptions.push(reporter);
 
   // always register commands needed to control terraform-ls
@@ -102,7 +102,11 @@ export async function activate(context: vscode.ExtensionContext): Promise<void>
     initializationFailedHandler: (error: ResponseError<InitializeError> | Error) => {
       initializationError = error;
 
-      reporter.sendTelemetryException(error);
+      reporter.sendTelemetryErrorEvent('initializationError', {
+        message: error.message,
+        stack: error.stack,
+        code: error instanceof ResponseError ? error.code.toString() : undefined,
+      });
 
       let msg = 'Failure to start terraform-ls. Please check your configuration settings and reload this window';
 
@@ -235,12 +239,17 @@ export async function deactivate(): Promise<void> {
   } catch (error) {
     if (error instanceof Error) {
       outputChannel.appendLine(error.message);
-      reporter.sendTelemetryException(error);
+      reporter.sendTelemetryErrorEvent('deactivate', {
+        message: error.message,
+        stack: error.stack,
+      });
       vscode.window.showErrorMessage(error.message);
       lsStatus.setLanguageServerState(error.message, false, vscode.LanguageStatusSeverity.Error);
     } else if (typeof error === 'string') {
       outputChannel.appendLine(error);
-      reporter.sendTelemetryException(new Error(error));
+      reporter.sendTelemetryErrorEvent('deactivate', {
+        message: error,
+      });
       vscode.window.showErrorMessage(error);
       lsStatus.setLanguageServerState(error, false, vscode.LanguageStatusSeverity.Error);
     }
diff --git a/src/features/telemetry.ts b/src/features/telemetry.ts
index 02197a42c..57f44892e 100644
--- a/src/features/telemetry.ts
+++ b/src/features/telemetry.ts
@@ -52,7 +52,11 @@ export class TelemetryFeature implements StaticFeature {
           return;
         }
 
-        this.reporter.sendRawTelemetryEvent(event.name, event.properties);
+        const thing: Record<string, string> = {};
+        for (const [key, value] of Object.entries(event.properties)) {
+          thing[key] = String(value);
+        }
+        this.reporter.sendRawTelemetryEvent(event.name, thing);
       }),
     );
   }
diff --git a/src/providers/tfc/applyProvider.ts b/src/providers/tfc/applyProvider.ts
index 8d5a7019d..8d54729d1 100644
--- a/src/providers/tfc/applyProvider.ts
+++ b/src/providers/tfc/applyProvider.ts
@@ -164,7 +164,10 @@ export class ApplyTreeDataProvider implements vscode.TreeDataProvider<vscode.Tre
       if (error instanceof Error) {
         message += error.message;
         vscode.window.showErrorMessage(message);
-        this.reporter.sendTelemetryException(error);
+        this.reporter.sendTelemetryErrorEvent('applyLogError', {
+          message: message,
+          stack: error.stack,
+        });
         return;
       }
 
diff --git a/src/providers/tfc/authenticationProvider.ts b/src/providers/tfc/authenticationProvider.ts
index a17b24e27..eeaaef1e1 100644
--- a/src/providers/tfc/authenticationProvider.ts
+++ b/src/providers/tfc/authenticationProvider.ts
@@ -93,10 +93,16 @@ class TerraformCloudSessionHandler {
         if ((error.response.status as number) === 401) {
           throw new InvalidToken();
         }
-        this.reporter.sendTelemetryException(error);
+        this.reporter.sendTelemetryErrorEvent('storeSession', {
+          message: error.message,
+          stack: error.stack,
+        });
         throw new Error(`Failed to login: ${apiErrorsToString(error.response.data.errors)}`);
       } else if (error instanceof Error) {
-        this.reporter.sendTelemetryException(error);
+        this.reporter.sendTelemetryErrorEvent('storeSession', {
+          message: error.message,
+          stack: error.stack,
+        });
       }
 
       throw error;
@@ -243,11 +249,16 @@ export class TerraformCloudAuthenticationProvider implements vscode.Authenticati
         return this.createSession(_scopes);
       } else if (error instanceof Error) {
         vscode.window.showErrorMessage(error.message);
-        this.reporter.sendTelemetryException(error);
+        this.reporter.sendTelemetryErrorEvent('invalidHCPToken', {
+          message: error.message,
+          stack: error.stack,
+        });
         this.logger.error(error.message);
       } else if (typeof error === 'string') {
         vscode.window.showErrorMessage(error);
-        this.reporter.sendTelemetryException(new Error(error));
+        this.reporter.sendTelemetryErrorEvent('invalidHCPToken', {
+          message: error,
+        });
         this.logger.error(error);
       }
 
diff --git a/src/providers/tfc/organizationPicker.ts b/src/providers/tfc/organizationPicker.ts
index 6785a5d1c..c4d332f06 100644
--- a/src/providers/tfc/organizationPicker.ts
+++ b/src/providers/tfc/organizationPicker.ts
@@ -100,10 +100,16 @@ export class OrganizationAPIResource implements APIResource {
         return picks;
       } else if (isErrorFromAlias(apiClient.api, 'listOrganizations', error)) {
         message += apiErrorsToString(error.response.data.errors);
-        this.reporter.sendTelemetryException(error);
+        this.reporter.sendTelemetryErrorEvent('orgranizationFetchError', {
+          message: message,
+          stack: error.stack,
+        });
       } else if (error instanceof Error) {
         message += error.message;
-        this.reporter.sendTelemetryException(error);
+        this.reporter.sendTelemetryErrorEvent('orgranizationFetchError', {
+          message: message,
+          stack: error.stack,
+        });
       } else if (typeof error === 'string') {
         message += error;
       }
diff --git a/src/providers/tfc/planProvider.ts b/src/providers/tfc/planProvider.ts
index 506906bf3..33e145c51 100644
--- a/src/providers/tfc/planProvider.ts
+++ b/src/providers/tfc/planProvider.ts
@@ -186,7 +186,10 @@ export class PlanTreeDataProvider implements vscode.TreeDataProvider<vscode.Tree
       if (error instanceof Error) {
         message += error.message;
         vscode.window.showErrorMessage(message);
-        this.reporter.sendTelemetryException(error);
+        this.reporter.sendTelemetryErrorEvent('planLogError', {
+          message: message,
+          stack: error.stack,
+        });
         return;
       }
 
diff --git a/src/providers/tfc/runProvider.ts b/src/providers/tfc/runProvider.ts
index 9ab3148e7..5e9245622 100644
--- a/src/providers/tfc/runProvider.ts
+++ b/src/providers/tfc/runProvider.ts
@@ -187,7 +187,10 @@ export class RunTreeDataProvider implements vscode.TreeDataProvider<TFCRunTreeIt
         if (isErrorFromAlias(apiClient.api, 'listRuns', error)) {
           message += apiErrorsToString(error.response.data.errors);
           vscode.window.showErrorMessage(message);
-          this.reporter.sendTelemetryException(error);
+          this.reporter.sendTelemetryErrorEvent('runProviderError', {
+            message: message,
+            stack: error.stack,
+          });
           return [];
         }
       }
@@ -195,7 +198,10 @@ export class RunTreeDataProvider implements vscode.TreeDataProvider<TFCRunTreeIt
       if (error instanceof Error) {
         message += error.message;
         vscode.window.showErrorMessage(message);
-        this.reporter.sendTelemetryException(error);
+        this.reporter.sendTelemetryErrorEvent('runProviderError', {
+          message: message,
+          stack: error.stack,
+        });
         return [];
       }
 
diff --git a/src/providers/tfc/uiHelpers.ts b/src/providers/tfc/uiHelpers.ts
index 16c9997b1..4034774cb 100644
--- a/src/providers/tfc/uiHelpers.ts
+++ b/src/providers/tfc/uiHelpers.ts
@@ -82,7 +82,10 @@ export async function handleZodiosError(
   outputChannel: vscode.OutputChannel,
   reporter: TelemetryReporter,
 ) {
-  reporter.sendTelemetryException(error);
+  reporter.sendTelemetryErrorEvent('zodiosError', {
+    message: error.message,
+    stack: error.stack,
+  });
   outputChannel.append(JSON.stringify({ cause: error.cause }, undefined, 2));
   const chosenItem = await vscode.window.showErrorMessage(
     `${msgPrefix} Response validation failed. Please report this as a bug.`,
diff --git a/src/providers/tfc/workspaceFilters.ts b/src/providers/tfc/workspaceFilters.ts
index 2b3ea5a6e..2ef4a2283 100644
--- a/src/providers/tfc/workspaceFilters.ts
+++ b/src/providers/tfc/workspaceFilters.ts
@@ -80,10 +80,16 @@ export class ProjectsAPIResource implements APIResource {
         return picks;
       } else if (isErrorFromAlias(apiClient.api, 'listProjects', error)) {
         message += apiErrorsToString(error.response.data.errors);
-        this.reporter.sendTelemetryException(error);
+        this.reporter.sendTelemetryErrorEvent('projectWorkspaceFetchError', {
+          message: message,
+          stack: error.stack,
+        });
       } else if (error instanceof Error) {
         message += error.message;
-        this.reporter.sendTelemetryException(error);
+        this.reporter.sendTelemetryErrorEvent('projectWorkspaceFetchError', {
+          message: message,
+          stack: error.stack,
+        });
       } else if (typeof error === 'string') {
         message += error;
       }
diff --git a/src/providers/tfc/workspaceProvider.ts b/src/providers/tfc/workspaceProvider.ts
index 35b339804..69fc95545 100644
--- a/src/providers/tfc/workspaceProvider.ts
+++ b/src/providers/tfc/workspaceProvider.ts
@@ -258,7 +258,10 @@ export class WorkspaceTreeDataProvider implements vscode.TreeDataProvider<vscode
         ) {
           message += apiErrorsToString(error.response.data.errors);
           vscode.window.showErrorMessage(message);
-          this.reporter.sendTelemetryException(error);
+          this.reporter.sendTelemetryErrorEvent('workspaceProviderError', {
+            message: message,
+            stack: error.stack,
+          });
           return [];
         }
       }
@@ -266,7 +269,10 @@ export class WorkspaceTreeDataProvider implements vscode.TreeDataProvider<vscode
       if (error instanceof Error) {
         message += error.message;
         vscode.window.showErrorMessage(message);
-        this.reporter.sendTelemetryException(error);
+        this.reporter.sendTelemetryErrorEvent('workspaceProviderError', {
+          message: message,
+          stack: error.stack,
+        });
         return [];
       }
 
diff --git a/src/utils/vscode.ts b/src/utils/vscode.ts
index 4b82f8d73..ec2705176 100644
--- a/src/utils/vscode.ts
+++ b/src/utils/vscode.ts
@@ -83,10 +83,15 @@ export async function handleLanguageClientStartError(
     return;
   } else if (error instanceof Error) {
     message = error.message;
-    reporter.sendTelemetryException(error);
+    reporter.sendTelemetryErrorEvent('extensionStartError', {
+      message: message,
+      stack: error.stack,
+    });
   } else if (typeof error === 'string') {
     message = error;
-    reporter.sendTelemetryException(new Error(error));
+    reporter.sendTelemetryErrorEvent('extensionStartError', {
+      message: error,
+    });
   }
 
   if (message === 'INVALID_URI_WSL') {
diff --git a/src/web/extension.ts b/src/web/extension.ts
index 5e2659c61..ca72cf345 100644
--- a/src/web/extension.ts
+++ b/src/web/extension.ts
@@ -12,7 +12,7 @@ let reporter: TelemetryReporter;
 
 export function activate(context: vscode.ExtensionContext) {
   const manifest = context.extension.packageJSON;
-  reporter = new TelemetryReporter(context.extension.id, manifest.version, manifest.appInsightsKey);
+  reporter = new TelemetryReporter(manifest.appInsightsKey);
   context.subscriptions.push(reporter);
   context.subscriptions.push(outputChannel);