Boring Toolbox Shows 500 / 500.19 Internal Server Error (IIS)

Symptoms

When accessing Boring Toolbox, the page fails to load and shows one of the following:

• 500 – Internal Server Error

• HTTP Error 500.19 – Internal Server Error
  “The requested page cannot be accessed because the related configuration data for the page is invalid.”

This typically occurs immediately after installation or upgrade.

Quick Decision Flow (Start Here)

Step 1 – Check URL Rewrite in IIS

• If URL Rewrite is missing or not visible → Go to Solution 1

• If URL Rewrite is present → Go to Step 2

Step 2 – Check IIS Application Paths

• If Physical Path does not match install location → Go to Solution 2

• If paths are correct → Contact Support

Solution 1: Reinstall IIS URL Rewrite Module

Use this solution if:

• URL Rewrite does not appear in IIS

• You see a 500 or 500.19 error referencing web.config

Steps

1. Open IIS Manager

2. Navigate to:

   Sites > Default Web Site
   

3. Look for URL Rewrite

📸 Screenshot Placeholder – URL Rewrite Missing

4. Open Add or Remove Programs

5. Locate IIS URL Rewrite Module

6. Uninstall it

7. Download and reinstall URL Rewrite 2.0:
   https://www.iis.net/downloads/microsoft/url-rewrite

8. Reopen IIS and refresh Boring Toolbox

Expected Result

• Boring Toolbox loads normally

• No 500 / 500.19 error

Solution 2: Fix IIS Application Physical Path

Use this solution if:

• URL Rewrite is installed

• Error 500.19 still occurs

• Boring Toolbox or API paths are incorrect (common after upgrades)

Step A: Fix Boring Toolbox Path

1. Open IIS Manager

2. Navigate to:

   Sites > Default Web Site > BoringToolbox
   

3. Right-click BoringToolbox

4. Select:

   Manage Application > Advanced Settings
   

5. Update Physical Path to the installation path (Default below):

   C:\Program Files\The Boring Lab\Boring Toolbox Web
   

6. Click OK

📸 Screenshot Placeholder – IIS Physical Path (BoringToolbox)

Step B: Fix Boring API Path (If Present)

Repeat the same steps for BoringAPI and verify the installation path is correct (Default below):

C:\Program Files\The Boring Lab\Boring API

📸 Screenshot Placeholder – IIS Physical Path (BoringAPI)

Final Validation

After applying the fix:

1. Refresh the Boring Toolbox URL

2. Confirm the login page loads

3. Log in successfully

4. Activate the license

5. Convert sites to Managed Sites

6. Verify the dashboard loads correctly

Notes

• This issue most often occurs after upgrades

• IIS does not automatically update paths if the install directory was changed

• Always verify:

  • URL Rewrite module

  • IIS Physical Paths

  • Correct install directories