diff --git a/package.json b/package.json
index effb14c1..bf003f85 100644
--- a/package.json
+++ b/package.json
@@ -115,6 +115,11 @@
                 "command": "azure-pipelines.configure-pipeline",
                 "title": "Configure Pipeline",
                 "category": "Azure Pipelines"
+            },
+            {
+                "command": "azure-pipelines.reset-state",
+                "title": "Reset 'do not ask again' messages",
+                "category": "Azure Pipelines"
             }
         ],
         "menus": {
diff --git a/src/extension.ts b/src/extension.ts
index 71e1def0..b24482c4 100644
--- a/src/extension.ts
+++ b/src/extension.ts
@@ -8,7 +8,7 @@ import * as vscode from 'vscode';
 import * as languageclient from 'vscode-languageclient/node';
 
 import * as logger from './logger';
-import { getSchemaAssociation, locateSchemaFile, onDidSelectOrganization, SchemaAssociationNotification } from './schema-association-service';
+import { getSchemaAssociation, locateSchemaFile, onDidSelectOrganization, resetDoNotAskState, SchemaAssociationNotification } from './schema-association-service';
 import { schemaContributor, CUSTOM_SCHEMA_REQUEST, CUSTOM_CONTENT_REQUEST } from './schema-contributor';
 import { telemetryHelper } from './helpers/telemetryHelper';
 import { getAzureAccountExtensionApi } from './extensionApis';
@@ -115,6 +115,8 @@ async function activateYmlContributor(context: vscode.ExtensionContext) {
     context.subscriptions.push(onDidSelectOrganization(async workspaceFolder => {
         await loadSchema(context, client, workspaceFolder);
     }));
+
+    context.subscriptions.push(vscode.commands.registerCommand("azure-pipelines.reset-state", async () => await resetDoNotAskState(context)));
 }
 
 // Find the schema and notify the server.
diff --git a/src/schema-association-service.ts b/src/schema-association-service.ts
index 7f9a3df8..67c5c569 100644
--- a/src/schema-association-service.ts
+++ b/src/schema-association-service.ts
@@ -28,8 +28,17 @@ export const onDidSelectOrganization = selectOrganizationEvent.event;
 const seenOrganizations = new Set<string>();
 const lastUpdated1ESPTSchema = new Map<string, Date>();
 
+export const DO_NOT_ASK_SIGN_IN_KEY = "DO_NOT_ASK_SIGN_IN_KEY";
+export const DO_NOT_ASK_SELECT_ORG_KEY = "DO_NOT_ASK_SELECT_ORG_KEY";
+
 let repoId1espt: string | undefined = undefined;
 
+export async function resetDoNotAskState(context: vscode.ExtensionContext) {
+    await context.globalState.update(DO_NOT_ASK_SIGN_IN_KEY, undefined);
+    await context.globalState.update(DO_NOT_ASK_SELECT_ORG_KEY, undefined);
+    logger.log("State is reset");
+}
+
 export async function locateSchemaFile(
     context: vscode.ExtensionContext,
     workspaceFolder: vscode.WorkspaceFolder | undefined): Promise<string> {
@@ -105,6 +114,12 @@ async function autoDetectSchema(
     // can't return until the sessions are also available.
     // This only returns false if there is no login.
     if (!(await azureAccountApi.waitForSubscriptions())) {
+        const doNotAskAgainSignIn = context.globalState.get<boolean>(DO_NOT_ASK_SIGN_IN_KEY);
+        if (doNotAskAgainSignIn) {
+            logger.log(`Not prompting for login - do not ask again was set`, 'SchemaDetection');
+            return undefined;
+        }
+    
         logger.log(`Waiting for login`, 'SchemaDetection');
 
         try {
@@ -117,7 +132,7 @@ async function autoDetectSchema(
 
         // Don't await this message so that we can return the fallback schema instead of blocking.
         // We'll detect the login in extension.ts and then re-request the schema.
-        void vscode.window.showInformationMessage(Messages.signInForEnhancedIntelliSense, Messages.signInLabel)
+        void vscode.window.showInformationMessage(Messages.signInForEnhancedIntelliSense, Messages.signInLabel, Messages.doNotAskAgain)
             .then(async action => {
                 if (action === Messages.signInLabel) {
                     await vscode.window.withProgress({
@@ -126,6 +141,8 @@ async function autoDetectSchema(
                     }, async () => {
                         await vscode.commands.executeCommand("azure-account.login");
                     });
+                } else if (action === Messages.doNotAskAgain) {
+                    await context.globalState.update(DO_NOT_ASK_SIGN_IN_KEY, true);
                 }
             });
 
@@ -190,6 +207,12 @@ async function autoDetectSchema(
                 `Using cached information for ${workspaceFolder.name}: ${organizationName}, ${session?.tenantId}`,
                 'SchemaDetection');
         } else {
+            const doNotAskAgainSelectOrg = context.globalState.get<boolean>(DO_NOT_ASK_SELECT_ORG_KEY);
+            if (doNotAskAgainSelectOrg) {
+                logger.log(`Not prompting for organization - do not ask again was set`, 'SchemaDetection');
+                return;
+            }
+
             logger.log(`Prompting for organization for ${workspaceFolder.name}`, 'SchemaDetection');
 
             // Otherwise, we need to manually prompt.
@@ -199,7 +222,7 @@ async function autoDetectSchema(
             // We'll detect when they choose the organization in extension.ts and then re-request the schema.
             void vscode.window.showInformationMessage(
                 format(Messages.selectOrganizationForEnhancedIntelliSense, workspaceFolder.name),
-                Messages.selectOrganizationLabel)
+                Messages.selectOrganizationLabel, Messages.doNotAskAgain)
                 .then(async action => {
                     if (action === Messages.selectOrganizationLabel) {
                         // Lazily construct list of organizations so that we can immediately show the quick pick,
@@ -237,6 +260,8 @@ async function autoDetectSchema(
                         });
 
                         selectOrganizationEvent.fire(workspaceFolder);
+                    } else if (action === Messages.doNotAskAgain) {
+                        await context.globalState.update(DO_NOT_ASK_SELECT_ORG_KEY, true);
                     }
                 });
             return undefined;