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Table of Contents

Checkpoint VPN Client Download

Image result for checkpoint vpn logo

Overview

CheckPoint is an application installed on your computer that connects virtually connects you to the Oakland Schools network. 

Once downloaded and installed, staff will log in with their FULL email address and email address password. 

Troubleshooting Issues

Listed below are some common checkpoint VPN related issues you may encounter.

Unable to Connect / Double Duo Pushes

Attempt to connect to both the primary and secondary VPN server. For further assistance with this, navigate to:

Access Denied - Wrong Username or Password

  • Make sure you have DUO setup properly, and accept the notification on your phone. You will get this message if you don't accept it in time. Keep your application open and do not rely on the notification.

  • Use your email address as your username instead of oslan\username

  • Double check your username and password is correct.

VPN disconnecting every few minutes

This can happen sometimes if your computer falls asleep while connected to the VPN. This can be resolved by manually disconnecting from the VPN and then reconnecting.


Connecting to Checkpoint VPN

Microsoft Windows


OS VPN with CheckPoint makes use of DUO Two Factor Authentication. Make sure you have configured DUO. Further instructions here.

  • Make sure you are connected to the internet.
  • Open 'CheckPoint Endpoint Security VPN'.

    • At the lower right of your screen, click on the arrow to expand your system tray. Double-click on CheckPoint which looks like a yellow padlock.
    • If it's not currently in your 'System Tray', proceed to the next step.


Expand your task bar screenshot Windows 10


If you were able to find the icon on your 'System Tray', skip this step.

  • Open your 'Start Menu' in the lower left hand corner of your screen.
  • Begin typing 'Check Point Endpoint' and verify that the application is installed.
  • If you were able to locate it through this method, click on the application to open it and proceed as normal.

If you are still unable to find it, please follow the install instructions at the bottom of the page.

Find Check Point VPN icon screen shot Windows 10


  • Login with your username with your Oakland Schools E-Mail and password.
    • Make sure you use your original OS e-mail, NOT any email aliases
    • If OS e-mail is still giving you troubles, use oslan\LastNameFirstInitial
  • Select the Connect Button.
  • CheckPoint will now be waiting for you to confirm this request via DUO.

This uses which ever authentication you set up when you set up DUO Mobile originally. If you would like to change your authentication method, click here for more information.

  • Once you authenticate in Duo Mobile, will be logged into VPN. You will see a green circle on the yellow padlock icon.



  • To disconnect from the VPN, right click the padlock icon and select Disconnect.

Disconnect from the VPN when you are not using resources that require its use. This will free up connections during peak times, as well as assist with any latency that is introduced from a large amount of users.

Check Point VPN Disconnect screen shot




Apple Mac OS

OS VPN with CheckPoint makes use of DUO Two Factor Authentication. Make sure you have configured DUO. Further instructions here.

  1. Make sure you are connected to the internet

  2. Open CheckPoint.


At the top of your screen, click on the lock icon. Click on connect.

If there is no lock icon, open your launchpad and click 'Endpoint Security VPN'.

When asked to configure a new site, click 'Yes'

At the site wizard screen, select 'Next'.

When asked for server address or name, input the following: access2.oakland.k12.mi.us

Select 'Next'.

Select 'Trust and Continue'

Authentication method will be username and password

Once the site wizard is done, select 'Finish'.

  • Login with your username with your Oakland Schools E-Mail and password.
    • Make sure you use your original OS e-mail, NOT any email aliases
    • If OS e-mail is still giving you troubles, use oslan\LastNameFirstInitial
    • Use the same password you use to login on your computer/laptop and access email.
  • Select the Connect Button.
  • CheckPoint will now be waiting for you to confirm this request via DUO. This uses which ever authentication you set up when you set up DUO. Further instructions here.
  • You will be logged into VPN. You will see a green circle on the padlock icon.


  • To disconnect from the VPN, click the padlock icon and select disconnect.

Disconnect from the VPN when you are not using resources that require its use. This will free up connections during peak times, as well as assist with any latency that is introduced from a large amount of users.


Installing Checkpoint VPN

Microsoft Windows

  1. Click here to download the CheckPoint VPN installer.   

  2. Open the file OSVPN-W10.msi

    1. Click “Next” to continue.

  3. Accept the terms and click“Next”.

  4. Click “Install”.

  5. The installation is in progress.

  6. Click “Finish” when the installation completed.

  7. Restart the PC.

  8. After the PC boot up continue with the connecting instructions at the top of the page.

Figure 2.a

VPN Installation Windows Step One screen

Figure 3

VPN Installation Windows Step One screen - Terms and Conditions

Figure 4

VPN Installation Windows Step Install Screen

Figure 5

VPN Installation Windows Progress Screen

Figure 6

VPN Installation Windows Finish screen

Figure 7

VPN Installation Windows Restart to complete screen



Apple Mac OS

  1. Click here to download checkpoint VPN on MAC

  2. Open the file Checkpoint-MAC.dmg

  3. Double click Checkpoint-MAC.dmg

  4. At the introduction, press continue.

  5. At the licence accept, press continue, then agree.

  6. At the installation type, press install.

  7. At the summary section, once the installation was successful, press close.

Figure 3

Figure 4

Figure 5

Figure 5

Figure 7


Configuring Check Point VPN

Adding VPN Site Servers

  1. At the lower right of your screen, click on the arrow to expand your system tray. 
  2. Right click on the yellow padlock and click VPN Options
  3. Click NEW and both of these servers:
    1. access.oakland.k12.mi.us
    2. access2.oakland.k12.mi.us
    3. Preconfigured versions of VPN will have these named OS VPN Server 1/2)
  4. If the NEW button is grayed out, you must update your VPN version.
    1. Navigate to the top middle of this page, under Checkpoint VPN Client Downloads click on the button for your OS (Windows 10 or Mac OS)
    2. Once the download has finished, follow the respective guide for installing checkpoint:
      1. Installing Checkpoint VPN - Microsoft Windows 10
      2. Installing Checkpoint VPN - Apple Mac OS


Changing VPN Site Servers

  1. At the lower right of your screen, click on the arrow to expand your system tray.
  2. Right click the yellow padlock and click Connect To
  3. At the top, click the dropdown next to SITE and select the VPN site server you wish to use. If logging into one does not work for you, try the other.


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