diff --git a/.changeset/real-boats-promise.md b/.changeset/real-boats-promise.md
new file mode 100644
index 00000000000..8769bcdb667
--- /dev/null
+++ b/.changeset/real-boats-promise.md
@@ -0,0 +1,5 @@
+---
+"@clerk/upgrade": minor
+---
+
+Enhancing error handling throughout the SDK upgrade flow
diff --git a/packages/upgrade/src/app.js b/packages/upgrade/src/app.js
index ee181f62fa1..10b9bff4427 100644
--- a/packages/upgrade/src/app.js
+++ b/packages/upgrade/src/app.js
@@ -63,12 +63,7 @@ export default function App(props) {
 
   // Handle the individual SDK upgrade
   if (!fromVersion && !toVersion && sdks[0] === 'nextjs') {
-    return (
-      <SDKWorkflow
-        packageManager={props.packageManager}
-        sdk={sdks[0]}
-      />
-    );
+    return <SDKWorkflow sdk={sdks[0]} />;
   }
 
   // We try to guess which SDK they are using
diff --git a/packages/upgrade/src/cli.js b/packages/upgrade/src/cli.js
index 78ad8769b33..da191342805 100644
--- a/packages/upgrade/src/cli.js
+++ b/packages/upgrade/src/cli.js
@@ -17,7 +17,6 @@ const cli = meow(
       --sdk              Name of the SDK you're upgrading
       --dir              Directory you'd like to scan for files
       --ignore           Any files or directories you'd like to ignore
-      --packageManager   The package manager you're using (npm, yarn, pnpm)
       --noWarnings       Do not print warnings, only items that must be fixed
       --disableTelemetry Do not send anonymous usage telemetry
 
@@ -34,7 +33,6 @@ const cli = meow(
       sdk: { type: 'string', choices: sdks.map(i => i.value) },
       dir: { type: 'string' },
       ignore: { type: 'string', isMultiple: true },
-      packageManager: { type: 'string' },
       yolo: { type: 'boolean' },
       noWarnings: { type: 'boolean' },
       disableTelemetry: { type: 'boolean' },
diff --git a/packages/upgrade/src/components/Codemod.js b/packages/upgrade/src/components/Codemod.js
index 9350dd110ad..9498dd800f4 100644
--- a/packages/upgrade/src/components/Codemod.js
+++ b/packages/upgrade/src/components/Codemod.js
@@ -58,7 +58,7 @@ export function Codemod(props) {
         </>
       )}
 
-      {!result && !error && glob && <Spinner label={`Running @clerk/${sdk}</Text> codemod... ${transform}`} />}
+      {!result && !error && glob && <Spinner label={`Running @clerk/${sdk} codemod... ${transform}`} />}
       {result && (
         <>
           <StatusMessage variant='success'>
diff --git a/packages/upgrade/src/components/SDKWorkflow.js b/packages/upgrade/src/components/SDKWorkflow.js
index 4c734e18ca6..bf07c29f5c0 100644
--- a/packages/upgrade/src/components/SDKWorkflow.js
+++ b/packages/upgrade/src/components/SDKWorkflow.js
@@ -16,13 +16,12 @@ import { UpgradeSDK } from './UpgradeSDK.js';
  *
  * @component
  * @param {Object} props
- * @param {string} props.packageManager - The package manager to use for the upgrade, if needed.
  * @param {string} props.sdk - The SDK to be upgraded.
  *
  * @returns {JSX.Element} The rendered component.
  */
 export function SDKWorkflow(props) {
-  const { packageManager, sdk } = props;
+  const { sdk } = props;
 
   const [done, setDone] = useState(false);
   const [runCodemod, setRunCodemod] = useState(false);
@@ -59,7 +58,6 @@ export function SDKWorkflow(props) {
         <>
           <UpgradeSDK
             callback={setUpgradeComplete}
-            packageManager={packageManager}
             sdk={sdk}
           />
           {upgradeComplete ? (
diff --git a/packages/upgrade/src/components/UpgradeSDK.js b/packages/upgrade/src/components/UpgradeSDK.js
index 1f52fffbb25..1fc3f3113a7 100644
--- a/packages/upgrade/src/components/UpgradeSDK.js
+++ b/packages/upgrade/src/components/UpgradeSDK.js
@@ -1,7 +1,7 @@
-import { Spinner, StatusMessage } from '@inkjs/ui';
+import { Select, Spinner, StatusMessage } from '@inkjs/ui';
 import { execa } from 'execa';
 import { existsSync } from 'fs';
-import { Text } from 'ink';
+import { Newline, Text } from 'ink';
 import React, { useEffect, useState } from 'react';
 
 function detectPackageManager() {
@@ -11,13 +11,12 @@ function detectPackageManager() {
     return 'yarn';
   } else if (existsSync('pnpm-lock.yaml')) {
     return 'pnpm';
-  } else {
-    return 'npm';
   }
+  return undefined;
 }
 
 function upgradeCommand(sdk, packageManager) {
-  switch (packageManager || detectPackageManager()) {
+  switch (packageManager) {
     case 'yarn':
       return `yarn add @clerk/${sdk}@latest`;
     case 'pnpm':
@@ -33,39 +32,85 @@ function upgradeCommand(sdk, packageManager) {
  * @component
  * @param {Object} props
  * @param {Function} props.callback - The callback function to be called after the command execution.
- * @param {string} props.packageManager - The package manager used in the project in case we cannot detect it automatically.
  * @param {string} props.sdk - The SDK for which the upgrade command is run.
  * @returns {JSX.Element} The rendered component.
  *
  * @example
  * <UpgradeCommand sdk="example-sdk" callback={handleUpgrade} />
  */
-export function UpgradeSDK({ callback, packageManager, sdk }) {
+export function UpgradeSDK({ callback, sdk }) {
+  const [command, setCommand] = useState();
   const [error, setError] = useState();
+  const [packageManager, setPackageManager] = useState(detectPackageManager());
   const [result, setResult] = useState();
 
-  const command = upgradeCommand(sdk, packageManager);
-
   useEffect(() => {
+    if (!packageManager) {
+      return;
+    }
+    setCommand(previous => {
+      if (previous) {
+        return previous;
+      }
+      return upgradeCommand(sdk, packageManager);
+    });
+    if (!command) {
+      return;
+    }
+
     execa({ shell: true })`${command}`
       .then(res => {
         setResult(res);
-        callback(true);
       })
       .catch(err => {
         setError(err);
+      })
+      .finally(() => {
+        callback(true);
       });
-  }, [command]);
+  }, [command, packageManager, sdk]);
 
   return (
     <>
-      {!result && !error && <Spinner label={`Running upgrade command: ${command}`} />}
+      {packageManager ? null : (
+        <>
+          <Text>
+            We could not detect the package manager used in your project. Please select the package manager you are
+            using
+          </Text>
+          <Select
+            options={[
+              { label: 'npm', value: 'npm' },
+              { label: 'pnpm', value: 'pnpm' },
+              { label: 'yarn', value: 'yarn' },
+            ]}
+            onChange={setPackageManager}
+          />
+        </>
+      )}
+      {packageManager && !result && !error && <Spinner label={`Running upgrade command: ${command}`} />}
       {result && (
         <StatusMessage variant='success'>
           <Text bold>@clerk/{sdk}</Text> upgraded successfully to <Text bold>latest!</Text>
         </StatusMessage>
       )}
-      {error && <StatusMessage variant='error'>Upgrade failed!</StatusMessage>}
+      {error && (
+        <>
+          <StatusMessage variant='error'>
+            Running the upgrade command failed:{' '}
+            <Text
+              bold
+              color='red'
+            >
+              {command}
+            </Text>
+          </StatusMessage>
+          <StatusMessage variant='info'>
+            Please manually upgrade <Text bold>@clerk/{sdk}</Text> to <Text bold>latest</Text> in your project.
+          </StatusMessage>
+          <Newline />
+        </>
+      )}
     </>
   );
 }