diff --git a/src/funcCoreTools/getBrewPackageName.ts b/src/funcCoreTools/getBrewPackageName.ts
index 7a640a07a..21dee7190 100644
--- a/src/funcCoreTools/getBrewPackageName.ts
+++ b/src/funcCoreTools/getBrewPackageName.ts
@@ -5,7 +5,37 @@
 
 import { funcPackageName } from '../constants';
 import { FuncVersion, getMajorVersion } from '../FuncVersion';
+import { cpUtils } from '../utils/cpUtils';
 
 export function getBrewPackageName(version: FuncVersion): string {
     return `${funcPackageName}@${getMajorVersion(version)}`;
 }
+
+export async function tryGetInstalledBrewPackageName(version: FuncVersion): Promise<string | undefined> {
+    const brewPackageName: string = getBrewPackageName(version);
+    if (await isBrewPackageInstalled(brewPackageName)) {
+        return brewPackageName;
+    } else {
+        let oldPackageName: string | undefined;
+        if (version === FuncVersion.v2) {
+            oldPackageName = funcPackageName;
+        } else if (version === FuncVersion.v3) {
+            oldPackageName = funcPackageName + '-v3-preview';
+        }
+
+        if (oldPackageName && await isBrewPackageInstalled(oldPackageName)) {
+            return oldPackageName;
+        } else {
+            return undefined;
+        }
+    }
+}
+
+async function isBrewPackageInstalled(packageName: string): Promise<boolean> {
+    try {
+        await cpUtils.executeCommand(undefined, undefined, 'brew', 'ls', packageName);
+        return true;
+    } catch (error) {
+        return false;
+    }
+}
diff --git a/src/funcCoreTools/getFuncPackageManagers.ts b/src/funcCoreTools/getFuncPackageManagers.ts
index 560e5265b..e8207a329 100644
--- a/src/funcCoreTools/getFuncPackageManagers.ts
+++ b/src/funcCoreTools/getFuncPackageManagers.ts
@@ -6,7 +6,7 @@
 import { funcPackageName, PackageManager } from '../constants';
 import { FuncVersion } from '../FuncVersion';
 import { cpUtils } from '../utils/cpUtils';
-import { getBrewPackageName } from './getBrewPackageName';
+import { tryGetInstalledBrewPackageName } from './getBrewPackageName';
 
 export async function getFuncPackageManagers(isFuncInstalled: boolean): Promise<PackageManager[]> {
     const result: PackageManager[] = [];
@@ -35,14 +35,18 @@ export async function getFuncPackageManagers(isFuncInstalled: boolean): Promise<
 async function hasBrew(isFuncInstalled: boolean): Promise<boolean> {
     for (const version of Object.values(FuncVersion)) {
         if (version !== FuncVersion.v1) {
-            const brewPackageName: string = getBrewPackageName(version);
-            try {
-                isFuncInstalled ?
-                    await cpUtils.executeCommand(undefined, undefined, 'brew', 'ls', brewPackageName) :
+            if (isFuncInstalled) {
+                const packageName: string | undefined = await tryGetInstalledBrewPackageName(version);
+                if (packageName) {
+                    return true;
+                }
+            } else {
+                try {
                     await cpUtils.executeCommand(undefined, undefined, 'brew', '--version');
-                return true;
-            } catch (error) {
-                // an error indicates no brew
+                    return true;
+                } catch (error) {
+                    // an error indicates no brew
+                }
             }
         }
     }
diff --git a/src/funcCoreTools/uninstallFuncCoreTools.ts b/src/funcCoreTools/uninstallFuncCoreTools.ts
index bdd1d53c0..bf9eab39a 100644
--- a/src/funcCoreTools/uninstallFuncCoreTools.ts
+++ b/src/funcCoreTools/uninstallFuncCoreTools.ts
@@ -10,7 +10,7 @@ import { FuncVersion } from '../FuncVersion';
 import { localize } from '../localize';
 import { cpUtils } from '../utils/cpUtils';
 import { nonNullValue } from '../utils/nonNull';
-import { getBrewPackageName } from './getBrewPackageName';
+import { tryGetInstalledBrewPackageName } from './getBrewPackageName';
 import { getFuncPackageManagers } from './getFuncPackageManagers';
 import { tryGetLocalFuncVersion } from './tryGetLocalFuncVersion';
 
@@ -35,7 +35,7 @@ export async function uninstallFuncCoreTools(_context: IActionContext, packageMa
             break;
         case PackageManager.brew:
             const version: FuncVersion = nonNullValue(await tryGetLocalFuncVersion(), 'localFuncVersion');
-            const brewPackageName: string = getBrewPackageName(version);
+            const brewPackageName: string = nonNullValue(await tryGetInstalledBrewPackageName(version), 'brewPackageName');
             await cpUtils.executeCommand(ext.outputChannel, undefined, 'brew', 'uninstall', brewPackageName);
             break;
         default:
diff --git a/src/funcCoreTools/updateFuncCoreTools.ts b/src/funcCoreTools/updateFuncCoreTools.ts
index a57eed5fe..2aaa08045 100644
--- a/src/funcCoreTools/updateFuncCoreTools.ts
+++ b/src/funcCoreTools/updateFuncCoreTools.ts
@@ -8,7 +8,8 @@ import { ext } from '../extensionVariables';
 import { FuncVersion } from '../FuncVersion';
 import { localize } from '../localize';
 import { cpUtils } from '../utils/cpUtils';
-import { getBrewPackageName } from './getBrewPackageName';
+import { nonNullValue } from '../utils/nonNull';
+import { getBrewPackageName, tryGetInstalledBrewPackageName } from './getBrewPackageName';
 import { getNpmDistTag, INpmDistTag } from './getNpmDistTag';
 
 export async function updateFuncCoreTools(packageManager: PackageManager, version: FuncVersion): Promise<void> {
@@ -20,10 +21,16 @@ export async function updateFuncCoreTools(packageManager: PackageManager, versio
             break;
         case PackageManager.brew:
             const brewPackageName: string = getBrewPackageName(version);
-            await cpUtils.executeCommand(ext.outputChannel, undefined, 'brew', 'upgrade', brewPackageName);
+            const installedBrewPackageName: string = nonNullValue(await tryGetInstalledBrewPackageName(version), 'brewPackageName');
+            if (brewPackageName !== installedBrewPackageName) {
+                // Uninstall deprecated tag and install latest tag
+                await cpUtils.executeCommand(ext.outputChannel, undefined, 'brew', 'uninstall', installedBrewPackageName);
+                await cpUtils.executeCommand(ext.outputChannel, undefined, 'brew', 'install', brewPackageName);
+            } else {
+                await cpUtils.executeCommand(ext.outputChannel, undefined, 'brew', 'upgrade', brewPackageName);
+            }
             break;
         default:
             throw new RangeError(localize('invalidPackageManager', 'Invalid package manager "{0}".', packageManager));
-            break;
     }
 }
diff --git a/src/funcCoreTools/validateFuncCoreToolsIsLatest.ts b/src/funcCoreTools/validateFuncCoreToolsIsLatest.ts
index e7308bf50..7267339f2 100644
--- a/src/funcCoreTools/validateFuncCoreToolsIsLatest.ts
+++ b/src/funcCoreTools/validateFuncCoreToolsIsLatest.ts
@@ -38,6 +38,7 @@ export async function validateFuncCoreToolsIsLatest(): Promise<void> {
                 return;
             } else if (packageManagers.length === 1) {
                 packageManager = packageManagers[0];
+                context.telemetry.properties.packageManager = packageManager;
             } else {
                 context.telemetry.properties.multiFunc = 'true';
                 if (showMultiCoreToolsWarning) {