IIS Hosting

Website Documentation for your KeePass client and Pleasant Password Server

Hosting with IIS (Internet Information Services) provides a full management interface to configure the network traffic to your website.

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Benefits of IIS Hosting

IIS provides more features, scalability, & robustness than the lightweight IIS Express. IIS Express is a smaller, self-contained version, which is installed by default and starts as a task with the Pleasant Password Server service.

  • Allows more configuration
  • Allows for more authentication options, such as:
  • Additional logging options
  • etc.

Below are the migration steps, which in the future, will be replaced with a more automated solution.

Migration Steps From IIS Express to IIS

If PPASS is already installed skip to step 3.

Step 1: Copy your Application files to the IIS Machine

Do this step if you are migrating to a different machine running IIS. (Otherwise, skip to Step 2).

  • Copy the Registry entries:
    • On the IIS Express machine, open the Windows registry and expand the HKEY_LOCAL_MACHINE\SOFTWARE\Pleasant Solutions, right click on it, and click Export.
    • On the IIS machine locate the same same branch, right-click on it, and click Import.


  • Copy application folders from the IIS Express machine to the IIS machine:
    • C:\Program Files (x86)\Pleasant Solutions
    • C:\ProgramData\Pleasant Solutions\Password Server folders

Step 2: Install your Application on IIS

  • Install the Application on the IIS Machine (if it is not installed already):
    • Install Pleasant Password Server
    • Stop the "Pleasant Password Server" service
    • Disable the "Pleasant Password Server" service
      • Stopping/Disabling this service is stopping the IIS Express service which we will be replacing with the IIS site.

Step 3: Enable IIS Feature

If IIS is already installed and visible in the Server Manager, then skip to step 4.

  • Enable IIS feature, if it's not already:
    • Open Control Panel > Server Manager and enable IIS feature.

Step 4: Add IIS Features

  • Add 3 features

    1. Open the Server Manager > "Add Roles and Features" Wizard: Server Roles > Web Server (IIS) > Web Server > Application Development (click add features):

    2. Next download and install this feature:

      • URL Rewrite
        • Download URL Rewrite and install file from:
          • e.g. rewrite_amd64_en-US.msi 

Step 5: Create a New IIS Site

  • Select Sites > Add Website
  • Site name is for your own management
  • In the IIS Manager, create the new site and set the Physical path to:
    • C:\Program Files (x86)\Pleasant Solutions\Pleasant Password Server\www
  • Bind the site to type HTTPS
  • May choose to use a non-standard port such as 10001 (443 is also acceptable but be sure to match it in your service config), to limit traffic flowing to Password Server
  • Host name: Should be FQDN
  • Choose a SSL Certificate (needs to be uploaded to Pleasant Configuration Utility - we can use the placeholder if we aren't ready for this yet.)
  • Ensure "start website immediately" is unchecked

IIS Setup New Website

  • NOTE:
    • When switching from IIS Express service to our new IIS site, using the same hostname as in IIS Express will bring down the IIS Express site.
    • So alternatively we can first set a new hostname and then change it back when we are finally ready to make the switch-over.

Add Website Warning

Step 6: Configure the IIS Site

  • For the IIS site:
    • Click on the IIS website > Look on the right-hand side panel for:
      • Advanced Settings > (General) > 
      • Set Preload Enabled = True
      • Click Ok
  • IIS Manager Configuration
  • Now on the homepage on the left of the IIS console:
    • Click the IIS "Authentication" icon
      • For versions >= 7.9.0: Set ASP.NET Impersonation = Disabled
      • For versions < 7.9.0: Set ASP.NET Impersonation = Enabled

Step 7: Configure the IIS Application Pool User

IIS Manager

  • Select Application Pools under the homepage on the left of IIS console
  • Configure the account used for Password Server's "Application Pool"
    • Right-click on the Application Pool > Select "Advanced Settings" > Click Identity
      • Choose one of the following options:
        • Option A: LocalSystem (easiest)
        • Option B: Service Account (recommended)
        • Option C: ApplicationPoolIdentity (advanced)
  • Stay in the App Pool window and continue to step 7

Option A - LocalSystem (Easiest)

  • Uses the account which is the most powerful on the machine, with access privileges across the network

Option B - Service Account (Recommended)

  • A service account with Local Admin access (a local account or AD/LDAP account).


Option C - ApplicationPoolIdentity (Very Difficult Setup Steps)

Choosing this route will likely entail more challenging setup steps of account permissions.

  • Use a separate, unique Application Pool Identity
    • Explanation: This creates a new, virtual account to secure the application and it's communications in IIS an across the network with a custom, least privileged account (such as NetworkService). Rather than creating a new account for each application, this account will allow both: running in it's own space and connection to other network locations (e.g. Backup, and MS-SQL).
  • Set Identity = ApplicationPoolIdentity
  • Your new virtual user account can be referenced by this handle:

    • IIS APPPOOL\<YourApplicationPoolName>
    • This user will not be found by searching in your machine/network users
    • This user is only selected by referencing the "IIS APPPOOL\" location, indexed by the name of your application pool
  • (Note: in the next step 7, be sure to set Load User Profile = True)


Step 8: Configure the IIS Application Pool Settings

  • Application Pool > Select the application pool > Advanced Settings:

    • (General) > Start Mode = AlwaysRunning
      • Keep the website running
    • Process Model > Idle Time-out (minutes) = 0
      • Stop the website's App Pool from shutting down if it has been idle for awhile (after 20 minutes)
    • Process Model > Maximum Worker Processes = 0
      • Allow numerous processes at a time
    • * Process Model > Load User Profile = True
      • * Only needed if you are:
        • Using a Service Account or ApplicationPoolIdentity user, OR,
        • Seeing IsolatedStorage errors in server Logging Details

Step 9: Configure the User Account Permissions

  • Configure access on this Machine: 

    • If you have chosen a Local Admin account or LocalSystem:
      • Your account will have the permissions needed on this machine

    • Otherwise, provide access:

      • If using the ApplicationPoolIdentity, see how to reference this user in Step 6, Option A.

      • File Folders:

        • Give the account "modify" rights on these folders:
          • C:\Program Files (x86)\Pleasant Solutions
          • C:\ProgramData\Pleasant Solutions\Password Server
      • Registry Keys:

        • Give the account "Full Control" rights for the registry settings:
          • Expand the HKEY_LOCAL_MACHINE\SOFTWARE\Pleasant Solutions
          • Right-Click the folder > select Permissions... > select the Group or username > Advanced > Permissions tab
            • Select the Group or username > Click Add or View button
              • Type: Allow
              • Applies to: This key and subkeys (Replaces all child object permissions)
              • Must remove the permission "Write DAC" - without this the permissions will be reset at restart.
  • Configure Network Access:

    • This account may need access for the following connections:

      • Network Backups: if your Pleasant Password application automatic Backups are placed on a network share
      • MS SQL Server Database: give this same user (selected in step 6) access to your database instance
    • (Note: If using the ApplicationPoolIdentity, see how to reference this user in Step 6, Option A.)

Step 10: Start the IIS site

  1. If you have not done so, Stop the "Pleasant Password Server" service
    • Disable the "Pleasant Password Server" service

  2. Select Application Pool > Select site
    • Recycle the Application Pool

  3. The site will now appear under "sites" in the IIS console on the left
    • Click to Start the site (from the right-hand side panel)

  4. If necessary, reboot the server and restart IIS


Please Contact Us!  If you have any questions or any difficulties regarding these steps.


  • If the site does not start or you notice errors:
    • Check for error details in Windows Event Logs, or temporarily increase the IIS webpage error 500 details (see below for more info).

    • Increase the Server Logging Details, and check logging activity.


  • If you see "Requested registry access is not allowed"
    • There is an issue with permissions. Switch to using either: a Service account user with local admin on the server, or to the LocalSystem user.
    • Contact us and let us help resolve the issue.


  • If you see an error accessing Web.config file: 
    • There could be a couple potential problems:

      • 1) The Application Pool user (for this website) may not have the file folder permissions to access the web.config file.
        • - We would encourage using a User Service Account with local admin privileges to this machine, or the LocalSystem user.
        • - You may need to give the process running your web app the permissions explained in Step 6.
        • - Some customers are expressed difficulty using the "ApplicationPoolIdentity" virtual user, which are looking into
      • 2) If one of the necessary IIS Features has not been installed (explained in step 3):

              - URL Rewrite module
              - IIS: ASP.NET


  • If you receive an "IsolatedStorage" error:
    • Consider upgrading to the most recent stable or higher which better handles this.
    • Set "Load User Profile" = True   (step 7)


  • If you receive a "Method Not Allowed" error, when modifying an entry in KeePass for Pleasant client:
    • Remove the WebDAV feature from IIS, and reboot the server
      • Open Control Panel > All Control Panel Items > Programs and Features > Select Turn Windows features on or off
      • Uncheck the WebDAV feature:
        • Internet Information Services > World Wide Web Services > Common HTTP Features
      • Reboot and restart IIS server
      • Double check settings in step 6 as this reboot can sometimes affect this setup


  • If you notice the Application Pool starts and immediately stops:


  • If you see an 500 error in your browser, 
    • View this HTTP Error Codes for IIS page and lookup the 0x800 error code: eg. 0x8007000d 
    • Check that the 3 features listed at the start may are added:
      • in particular IIS: ASP.NET 
      • URL Rewrite 2.1 may need to be re-installed
    • Check for additional Logging detail errors or the windows Event logs.

Increasing Error 500 details:

If you are receiving an error 500 or 400 you can increase the details by following these steps:

HTTP error 500

Open the error pages:

IIS increase details

Edit the custom error page

IIS edit custom error