diff --git a/src/Console/Commands/ProEnable.php b/src/Console/Commands/ProEnable.php
index 865cc726d1..ed111c006d 100644
--- a/src/Console/Commands/ProEnable.php
+++ b/src/Console/Commands/ProEnable.php
@@ -40,6 +40,7 @@ public function handle()
         }
 
         $this->checkInfo('Statamic Pro successfully enabled in .env file!');
+        $this->promptToSetLicenseKey();
 
         if ($this->option('update-config') && $this->updateConfig()) {
             $this->checkInfo('Statamic editions config successfully updated to reference .env var!');
@@ -53,7 +54,7 @@ public function handle()
             $this->crossLine('Statamic editions config not currently referencing .env var!');
             $this->comment('Please re-run this command with the `--update-config` option.');
         } else {
-            $this->laravel['config']['statamic.editions.pro'] = true;
+            config()->set('statamic.editions.pro', true);
         }
     }
 
@@ -84,7 +85,7 @@ protected function setProInEnvironmentFile()
      */
     protected function proEnvVarExists()
     {
-        return preg_match('/^STATAMIC_PRO_ENABLED=/m', $this->envContents());
+        return preg_match('/^#?\s*STATAMIC_PRO_ENABLED=/m', $this->envContents());
     }
 
     /**
@@ -95,7 +96,7 @@ protected function proEnvVarExists()
     protected function ensureProInEnv()
     {
         file_put_contents($this->envPath(), preg_replace(
-            '/^STATAMIC_PRO_ENABLED=.*$/m',
+            '/^#?\s*STATAMIC_PRO_ENABLED=.*$/m',
             'STATAMIC_PRO_ENABLED=true',
             $this->envContents()
         ));
@@ -111,6 +112,98 @@ protected function appendProToEnv()
         file_put_contents($this->envPath(), $this->envContents()."\nSTATAMIC_PRO_ENABLED=true");
     }
 
+    /**
+     * Prompt to set the license key in the environment file.
+     *
+     * @return void
+     */
+    protected function promptToSetLicenseKey()
+    {
+        if (! $this->input->isInteractive()) {
+            return;
+        }
+
+        if ($this->licenseKeyAlreadySet()) {
+            return;
+        }
+
+        $licenseKey = trim((string) $this->ask('If you have a Statamic license key, paste it now (leave blank to add later)'));
+
+        if ($licenseKey === '') {
+            $this->comment('Add `STATAMIC_LICENSE_KEY=...` to your `.env` before or when your site goes live.');
+
+            return;
+        }
+
+        if ($this->licenseKeyEnvVarExists()) {
+            $this->replaceLicenseKeyInEnv($licenseKey);
+        } else {
+            $this->appendLicenseKeyToEnv($licenseKey);
+        }
+
+        $this->checkInfo('Statamic license key saved in .env file.');
+    }
+
+    /**
+     * Check whether a non-empty license key already exists.
+     *
+     * @return bool
+     */
+    protected function licenseKeyAlreadySet()
+    {
+        $licenseKey = $this->licenseKeyFromEnv();
+
+        return $licenseKey !== null && $licenseKey !== '';
+    }
+
+    /**
+     * Check whether the license key env var exists.
+     *
+     * @return bool
+     */
+    protected function licenseKeyEnvVarExists()
+    {
+        return preg_match('/^#?\s*STATAMIC_LICENSE_KEY=/m', $this->envContents());
+    }
+
+    /**
+     * Replace key in .env file.
+     *
+     * @param  string  $licenseKey
+     * @return void
+     */
+    protected function replaceLicenseKeyInEnv($licenseKey)
+    {
+        file_put_contents($this->envPath(), preg_replace_callback(
+            '/^#?\s*STATAMIC_LICENSE_KEY=.*$/m',
+            fn () => 'STATAMIC_LICENSE_KEY='.$licenseKey,
+            $this->envContents()
+        ));
+    }
+
+    /**
+     * Append key to end of .env file.
+     *
+     * @param  string  $licenseKey
+     * @return void
+     */
+    protected function appendLicenseKeyToEnv($licenseKey)
+    {
+        file_put_contents($this->envPath(), $this->envContents()."\nSTATAMIC_LICENSE_KEY={$licenseKey}");
+    }
+
+    /**
+     * Get the license key from .env.
+     *
+     * @return string|null
+     */
+    protected function licenseKeyFromEnv()
+    {
+        preg_match('/^STATAMIC_LICENSE_KEY=(.*)$/m', $this->envContents(), $matches);
+
+        return isset($matches[1]) ? trim($matches[1]) : null;
+    }
+
     /**
      * Get app .env path.
      *
@@ -118,7 +211,7 @@ protected function appendProToEnv()
      */
     protected function envPath()
     {
-        return $this->laravel->environmentFilePath();
+        return app()->environmentFilePath();
     }
 
     /**
diff --git a/tests/Console/Commands/ProEnableTest.php b/tests/Console/Commands/ProEnableTest.php
index 80c4045aa0..1679acf921 100644
--- a/tests/Console/Commands/ProEnableTest.php
+++ b/tests/Console/Commands/ProEnableTest.php
@@ -61,7 +61,9 @@ public function it_can_enable_pro_by_updating_existing_var_in_env()
         $this->assertEquals($this->defaultEditionsContents, $this->files->get($this->editionsPath));
         $this->assertEquals($this->defaultEnvContents, $this->files->get($this->envPath));
 
-        $this->artisan('statamic:pro:enable');
+        $this
+            ->artisan('statamic:pro:enable')
+            ->expectsQuestion('If you have a Statamic license key, paste it now (leave blank to add later)', '');
 
         $this->assertTrue(Statamic::pro());
         $this->assertEquals($this->defaultEditionsContents, $this->files->get($this->editionsPath));
@@ -83,7 +85,9 @@ public function it_can_enable_pro_by_appending_to_env()
         $this->assertFalse(Statamic::pro());
         $this->assertEquals($this->defaultEditionsContents, $this->files->get($this->editionsPath));
 
-        $this->artisan('statamic:pro:enable');
+        $this
+            ->artisan('statamic:pro:enable')
+            ->expectsQuestion('If you have a Statamic license key, paste it now (leave blank to add later)', '');
 
         $this->assertTrue(Statamic::pro());
         $this->assertEquals($this->defaultEditionsContents, $this->files->get($this->editionsPath));
@@ -94,6 +98,26 @@ public function it_can_enable_pro_by_appending_to_env()
 ENV, $this->files->get($this->envPath));
     }
 
+    #[Test]
+    public function it_replaces_commented_pro_enabled_var_in_env_instead_of_appending()
+    {
+        $this->files->put($this->envPath, <<<'ENV'
+APP_NAME=Statamic
+# STATAMIC_PRO_ENABLED=false
+STATAMIC_LICENSE_KEY=
+ENV);
+
+        $this
+            ->artisan('statamic:pro:enable')
+            ->expectsQuestion('If you have a Statamic license key, paste it now (leave blank to add later)', '');
+
+        $this->assertEquals(<<<'ENV'
+APP_NAME=Statamic
+STATAMIC_PRO_ENABLED=true
+STATAMIC_LICENSE_KEY=
+ENV, $this->files->get($this->envPath));
+    }
+
     #[Test]
     public function if_config_is_not_referencing_env_var_it_should_prompt_user_to_run_with_update_config_option()
     {
@@ -116,6 +140,7 @@ public function if_config_is_not_referencing_env_var_it_should_prompt_user_to_ru
 
         $this
             ->artisan('statamic:pro:enable')
+            ->expectsQuestion('If you have a Statamic license key, paste it now (leave blank to add later)', '')
             ->expectsOutput('Please re-run this command with the `--update-config` option.');
 
         // Though it should still update .env
@@ -159,7 +184,9 @@ public function it_can_update_editions_config_to_reference_env_var($boolean)
         $this->assertFalse(Statamic::pro());
         $this->assertEquals($this->defaultEnvContents, $this->files->get($this->envPath));
 
-        $this->artisan('statamic:pro:enable', ['--update-config' => true]);
+        $this
+            ->artisan('statamic:pro:enable', ['--update-config' => true])
+            ->expectsQuestion('If you have a Statamic license key, paste it now (leave blank to add later)', '');
 
         $this->assertTrue(Statamic::pro());
         $this->assertEquals($this->defaultEditionsContents, $this->files->get($this->editionsPath));
@@ -192,6 +219,7 @@ public function if_it_has_trouble_updating_editions_config_it_should_instruct_us
 
         $this
             ->artisan('statamic:pro:enable', ['--update-config' => true])
+            ->expectsQuestion('If you have a Statamic license key, paste it now (leave blank to add later)', '')
             ->expectsOutput(PHP_EOL.'For this setting to take effect, please modify your [config/statamic/editions.php] as follows:')
             ->expectsOutput("'pro' => env('STATAMIC_PRO_ENABLED', false)");
 
@@ -205,4 +233,79 @@ public function if_it_has_trouble_updating_editions_config_it_should_instruct_us
         // Pro should not be enabled in the in-memory config, because config is not properly referencing .env var yet
         $this->assertFalse(Statamic::pro());
     }
+
+    #[Test]
+    public function it_can_set_license_key_while_enabling_pro()
+    {
+        $this
+            ->artisan('statamic:pro:enable')
+            ->expectsQuestion('If you have a Statamic license key, paste it now (leave blank to add later)', 'test-license-key');
+
+        $this->assertEquals(<<<'ENV'
+APP_NAME=Statamic
+STATAMIC_PRO_ENABLED=true
+STATAMIC_LICENSE_KEY=test-license-key
+ENV, $this->files->get($this->envPath));
+    }
+
+    #[Test]
+    public function it_replaces_commented_license_key_line_instead_of_appending()
+    {
+        $this->files->put($this->envPath, <<<'ENV'
+APP_NAME=Statamic
+STATAMIC_PRO_ENABLED=false
+# STATAMIC_LICENSE_KEY=
+ENV);
+
+        $this
+            ->artisan('statamic:pro:enable')
+            ->expectsQuestion('If you have a Statamic license key, paste it now (leave blank to add later)', 'test-license-key');
+
+        $this->assertEquals(<<<'ENV'
+APP_NAME=Statamic
+STATAMIC_PRO_ENABLED=true
+STATAMIC_LICENSE_KEY=test-license-key
+ENV, $this->files->get($this->envPath));
+    }
+
+    #[Test]
+    public function commented_non_empty_license_key_still_prompts_and_gets_replaced()
+    {
+        $this->files->put($this->envPath, <<<'ENV'
+APP_NAME=Statamic
+STATAMIC_PRO_ENABLED=false
+# STATAMIC_LICENSE_KEY=overlord_698g7f6sd89gs
+ENV);
+
+        $this
+            ->artisan('statamic:pro:enable')
+            ->expectsQuestion('If you have a Statamic license key, paste it now (leave blank to add later)', 'test-license-key');
+
+        $this->assertEquals(<<<'ENV'
+APP_NAME=Statamic
+STATAMIC_PRO_ENABLED=true
+STATAMIC_LICENSE_KEY=test-license-key
+ENV, $this->files->get($this->envPath));
+    }
+
+    #[Test]
+    public function it_mentions_setting_license_key_later_when_left_blank()
+    {
+        $this
+            ->artisan('statamic:pro:enable')
+            ->expectsQuestion('If you have a Statamic license key, paste it now (leave blank to add later)', '')
+            ->expectsOutput('Add `STATAMIC_LICENSE_KEY=...` to your `.env` before or when your site goes live.');
+    }
+
+    #[Test]
+    public function it_skips_license_key_prompt_in_non_interactive_mode()
+    {
+        $this->artisan('statamic:pro:enable', ['--no-interaction' => true]);
+
+        $this->assertEquals(<<<'ENV'
+APP_NAME=Statamic
+STATAMIC_PRO_ENABLED=true
+STATAMIC_LICENSE_KEY=
+ENV, $this->files->get($this->envPath));
+    }
 }