Web Server Install of LeavePlanner.com Enterprise Edition

A typical installation should take no more than 10-15 minutes. If you encounter any errors during the installation then please double check the prerequisites to ensure you have the required hardware and software available. If your goal is simply to evaluate the features that are available in LeavePlanner.com then may we recommend that you request a trial of the online edition as the features are exactly the same.


  • Microsoft .NET Framework V4.8 or higher
  • Microsoft SQL Server 2012/SQLExpress or higher
  • Microsoft IIS v7.0 or higher with HTTP Activation Feature


The instructions below use the term WEBSITENAME. Replace WEBSITENAME with your domain name or something that makes sense in your network scenario.

File System

Create a folder on your web server where LeavePlanner will be deployed. For the remainder of these instructions we will assume this is C:\websites\WEBSITENAME, however, you are free to choose any suitable location.


If you are using IIS 7.5 (Windows 7/Windows Server 2008r2) you will need to complete this step after configuring the web server) You need to setup permissions on the C:\websites\WEBSITENAME folder.

To do this right click on the folder and choose Properties, then click on the Security tab on the properties window. Which account you add will depend on the version of IIS that you are using and this is generally dependent upon the version of Windows that you are running. Below is a list of the typical accounts you will use.

Windows Version IIS Version Account
Windows 2008 7.0 NETWORK SERVICE
Windows 2008 R2/2012 7.5 IIS APPPOOLWEBSITENAME

It is important to configure the appropriate account with permissions on the file system. Be sure that you are using a local machine account, not a domain account. If you have configured IIS and the Website Application Pools to run under a different user account than the defaults listed above configure permissions for that account. After adding the account to the list of users, click on the Read & Execute checkbox and APPLY the changes. Click OK to close the remaining open windows.

Repeat the above process for the C:\websites\WEBSITENAME\Images folder but this time give the user Full Control (this will allow you to upload your logo in the application)

Download LeavePlanner.com

You can download the latest release of LeavePlanner.com Enterprise Edition by clicking here. The package is delivered as a ZIP file.

Extract LeavePlanner.com

Depending on your operating system, some ZIP files require you to right click on the ZIP file, choose properties and then click on the UNBLOCK button on the properties windows. If you don’t have an UNBLOCK button you can ignore this step.

Extract the contents of the ZIP file to the C:\websites\WEBSITENAME folder. You can do this by right clicking on the file and choosing “Extract To”. If you browse C:\websites\WEBSITENAME with Windows Explorer and are able to see a file named web.config then the UNZIP was successful. If you do not see this file, the UNZIP was not successful and you either need to delete and re-do the extraction or move the extracted files into the C:\websites\WEBSITENAME folder.

Rename ConnectionStrings.config.dist to ConnectionStrings.config

Make the App_Data and images folder writable

Create the Website in IIS

Launch the IIS Management Console and create a new secure website (LeavePlanner must be accessed via the HTTPS protocol so you will need an SSL Certificate) pointing at the folder C:\websites\WEBSITENAME. Make sure you select the ASP.NET v4 Integrated Framework Application Pool for this new website. This completes the server side installation. The next step is performed in your web browser.

Launch the website in your browser

Launch the LeavePlanner website using the secure hostname you assigned to the new website. The website will guide you through the rest of the setup process.