diff --git a/Extension/package.json b/Extension/package.json
index cdfa82d47..73388edfc 100644
--- a/Extension/package.json
+++ b/Extension/package.json
@@ -3379,6 +3379,17 @@
                         "default": "default",
                         "markdownDescription": "%c_cpp.configuration.copilotHover.markdownDescription%",
                         "scope": "window"
+                    },
+                    "C_Cpp.windowsErrorReportingMode": {
+                        "type": "string",
+                        "enum": [
+                            "default",
+                            "enabled",
+                            "disabled"
+                        ],
+                        "default": "default",
+                        "markdownDescription": "%c_cpp.configuration.windowsErrorReportingMode.markdownDescription%",
+                        "scope": "window"
                     }
                 }
             }
diff --git a/Extension/package.nls.json b/Extension/package.nls.json
index 34295589f..c6bc95490 100644
--- a/Extension/package.nls.json
+++ b/Extension/package.nls.json
@@ -790,6 +790,12 @@
             "{Locked=\"`disabled`\"} {Locked=\"Copilot\"}"
         ]
     },
+    "c_cpp.configuration.windowsErrorReportingMode.markdownDescription": {
+        "message": "If `disabled`, Windows Error Reporting will be disabled. If `default`, Windows Error Reporting will be enabled, but it becomes disabled after the first crash in the current session. Changing the setting doesn't affect currently running IntelliSense processes.",
+        "comment": [
+            "{Locked=\"`disabled`\"} {Locked=\"`default`\"} {Locked=\"`IntelliSense`\"}"
+        ]
+    },
     "c_cpp.configuration.renameRequiresIdentifier.markdownDescription": {
         "message": "If `true`, 'Rename Symbol' will require a valid C/C++ identifier.",
         "comment": [
@@ -1084,4 +1090,4 @@
     "c_cpp.configuration.refactoring.includeHeader.never.description": "Never include the header file.",
     "c_cpp.languageModelTools.configuration.displayName": "C/C++ configuration",
     "c_cpp.languageModelTools.configuration.userDescription": "Configuration of the active C or C++ file, like language standard version and target platform."
-}
+}
\ No newline at end of file
diff --git a/Extension/src/LanguageServer/client.ts b/Extension/src/LanguageServer/client.ts
index d26655b0e..40611c728 100644
--- a/Extension/src/LanguageServer/client.ts
+++ b/Extension/src/LanguageServer/client.ts
@@ -90,6 +90,7 @@ export function hasTrustedCompilerPaths(): boolean {
 // Data shared by all clients.
 let languageClient: LanguageClient;
 let firstClientStarted: Promise<{ wasShutdown: boolean }>;
+let languageClientHasCrashed: boolean = false;
 let languageClientCrashedNeedsRestart: boolean = false;
 const languageClientCrashTimes: number[] = [];
 let compilerDefaults: configs.CompilerDefaults | undefined;
@@ -1600,6 +1601,7 @@ export class DefaultClient implements Client {
             codeAnalysisMaxMemory: workspaceSettings.codeAnalysisMaxMemory,
             codeAnalysisUpdateDelay: workspaceSettings.codeAnalysisUpdateDelay,
             copilotHover: workspaceSettings.copilotHover,
+            windowsErrorReportingMode: workspaceSettings.windowsErrorReportingMode,
             workspaceFolderSettings: workspaceFolderSettingsParams
         };
     }
@@ -1688,6 +1690,7 @@ export class DefaultClient implements Client {
             errorHandler: {
                 error: (_error, _message, _count) => ({ action: ErrorAction.Continue }),
                 closed: () => {
+                    languageClientHasCrashed = true;
                     languageClientCrashTimes.push(Date.now());
                     languageClientCrashedNeedsRestart = true;
                     let restart: boolean = true;
@@ -1752,6 +1755,12 @@ export class DefaultClient implements Client {
 
         if (usesCrashHandler()) {
             watchForCrashes(await languageClient.sendRequest(PreInitializationRequest, null));
+        } else if (os.platform() === "win32") {
+            const settings: CppSettings = new CppSettings();
+            if ((settings.windowsErrorReportingMode === "default" && !languageClientHasCrashed) ||
+                settings.windowsErrorReportingMode === "enabled") {
+                await languageClient.sendRequest(PreInitializationRequest, null);
+            }
         }
 
         // Move initialization to a separate message, so we can see log output from it.
diff --git a/Extension/src/LanguageServer/settings.ts b/Extension/src/LanguageServer/settings.ts
index 0f35cc315..6e199cd64 100644
--- a/Extension/src/LanguageServer/settings.ts
+++ b/Extension/src/LanguageServer/settings.ts
@@ -164,6 +164,7 @@ export interface SettingsParams {
     codeAnalysisUpdateDelay: number;
     workspaceFolderSettings: WorkspaceFolderSettingsParams[];
     copilotHover: string;
+    windowsErrorReportingMode: string;
 }
 
 function getTarget(): vscode.ConfigurationTarget {
@@ -478,6 +479,7 @@ export class CppSettings extends Settings {
         }
         return this.getAsString("copilotHover");
     }
+    public get windowsErrorReportingMode(): string { return this.getAsString("windowsErrorReportingMode"); }
     public get cppContextProviderParams(): string | undefined {
         const value = super.Section.get<any>("copilotContextProviderParams");
         if (isString(value)) {