There are a number of possible causes for such a behavior. This FAQ will help you to find out what is causing the problem in your specific situation. In this FAQ we will be using destination device as a generic term for the device you are trying to connect to. The destination device can be anything from a normal computer, to a server, to a network printer.

1. Are you trying to connect to the destination device using a host name?

If you are using a host name, please try once using its IP address instead. If that works, the problem has to do with DNS resolution. Please make sure DNS is enabled for the VPN connection and correctly configured. Note that using Bonjour or NETBIOS hostnames is generally not possible over VPN.

2. Is the IP address you are connecting to really part of the remote network?

For example, if your remote network is 192.168.13.0/24, you should be able to connect to IPs starting with 192.168.13.x, but connections to IPs starting with 192.168.14.x will not work as they are outside the address range of traffic tunneled through the VPN.

3. Is the local address in VPN Tracker part of the remote network?

Using a local address in VPN Tracker (Basic > Local Address) that is part of the remote network is not possible with most VPN gateways. Please use a local address that is outside all remote networks. For example, if your remote network is 192.168.13.0/24, do not use an address starting with 192.168.13. If you are using an automatic configuration method (e.g. Mode Config, EasyVPN, DHCP over VPN) you may be able to assign a local address to VPN Tracker that is part of the remote network. Refer to the configuration guide for your VPN gateway for more information.

4. Could multiple VPN users use the same local address?

If multiple VPN users exist, pleas make sure no two users are using the same local address (Basic > Local Address), otherwise one of them will not be able to use the tunnel anymore whenever both of them are connected. If that field is empty in your configuration, VPN Tracker will just use the IP address of your primary network interface as local address, and of course, this can also cause an address conflict with another user, that’s why we do not recommend to leave that field empty if there are multiple VPN users.

5. Can you ping the LAN address of the VPN gateway?

You can find a ping tool directly in VPN Tracker under Tools > Ping Host. The LAN address of the VPN gateway is special in the regard that this address doesn’t need to be routed at all. So if you can ping that address but no other remote address, it is most likely a routing issue at the remote end.

6. If you can't ping anything, try re-running the VPN Availability Test

The VPN Availability Test can be found in the menu: Tools > VPN Availability Test. Then try connecting the VPN again. The results of this test depend on the capabilities of your local Internet router/modem or the Internet connection itself and they influence how the VPN tunnel is established. VPN Tracker automatically runs the test for every new Internet connection it is able to detect but even if a connection has been tested before, there are various reasons why the behavior of that connection may have changed in the meantime.

7. Is your VPN gateway the default gateway (router) of its network?

If the VPN gateway is not the default gateway, you will in many cases need a suitable routing setup in order for responses to reach you. Whenever a device doesn’t know how to reach an IP address directly, it forwards its reply to its default gateway and if that isn’t the VPN gateway, it won’t know what to do with that reply data. In that case its important to configure the default gateway to forward replies to VPN users to the VPN gateway.

8. Is your VPN gateway the default gateway (router) of its network?

For more details, we would like to direct you to the following FAQ entry.

Configuring the Pre-Shared Key for a new VPN connection

I have lost my Pre-Shared Key - how can I get it back?

1. Check if you have stored the affected connection in your Personal Safe. If so, you may be able to download the connection again.
2. Check the Keychain (Applications > Utilities > Keychain Access). The Pre-Shared Key is usually saved here. Enter "Shared Secret" into the search bar to view a list of all your saved PSKs.
3. Are you using Time Machine Backup? You could try restoring an older connection with the Pre-Shared-Key.
4. Check your firewall or ask the relevant VPN Administrator. Refer to your device handbook to find out where to obtain this information on your specific firewall.

• Private IP Addresses, and
• Public IP Addresses

• 192.168.0.x, and
• 192.168.1.x

1. Change your local network to a different range (Preferred)

   
   Possible Ranges are:
   
   • 10.250.250.x
   • 172.30.30.x
   • 192.168.250.x
   
   Advantage: Once you have made this change on your home network, you will never have conflicts in this network.
   Disadvantage: You will need to change the settings on your private network router once, this requires access and can take some time.
   What to do:
   
   • Login to your home router
   • Find the setup section with “DHCP” settings.
   • Change your router to a different IP adress (for example an address from one of the ranges listed above, for example 172.30.30.1)
   • Change the DHCP Server Settings to the same range of your router (If your router IP is 172.30.30.1, your range could be 172.30.30.10 to 172.30.30.253){S_1183}
   
   After you have made these changes, there will be no more conflicts between your home and company network.{S_1184}

2. Force Traffic over VPN

   
   There may be situations where it's not possible to use the first option (for example if you're in a coffee shop or hotel) In this case you have the option to force the traffic over your VPN Network, this means your VPN Network (company network) will always win.
   Advantage: This setting is global, meaning no matter what network you are in you will always be able to connect.
   Disadvantage: Once you are connected to your company’s VPN, you can not access local service, like home router, local storages or printers.
   What to do:
   
   • Configure your VPN Tracker connection
   • Select the "Advanced" Tab at the top
   • In the "Traffic control" section, activate the Checkbox "Force traffic over the VPN if remote networks conflict with local networks"{S_1189}
   
   

Download VPN Tracker free

1. If you have connections or Shortcuts on your Mac that are stored in your Personal Safe, deactivate Personal Safe in preferences and create a local copy of your connections
2. Go to your Personal Safe webpage and delete your user keys: https://my.vpntracker.com/user/sync/keys
3. Sign out from your VPN Tracker account on your Mac, open Keychain Access, and delete the entry "Connection Safe Master Key."
4. Then sign back in and add a connection to your safe.
5. Don't forget to write down the new recovery key and keep it in a safe place. This will enable you to log in if you ever lose your login details.

VPN Tracker automatically stores a backup of all your VPN connections on your Mac. If you have inadvertently deleted a connection, or wish to revert to an earlier copy of a connection, you can manually restore the backup copy.

1. Turn off Personal Safe syncing

You need to deactivate Personal Safe for the connections you're trying to restore from your backup, to prevent unwanted changes being synced:

• Open VPN Tracker 365
• From the menu bar, choose: VPN Tracker 365 > Preferences > Personal Safe
• Uncheck the connections you want to restore from your backup
• Quit VPN Tracker 365

2. Restore from your Backup

• Open Finder and choose "Go" > "Go to Folder…" from the menu bar
• Enter this path and press Return:
  /Library/Application Support/VPN Tracker 365
• Rename your "etc" folder to "etc-backup" – for safekeeping
• Go into the "backup" folder

Here you'll see a number of backup folders, all organized and named by date.

• Move the "etc-date" folder you want to restore up one level into the main "VPN Tracker 365" folder
• Rename the folder your just moved to just "etc" (deleting the date)
• Open VPN Tracker 365

All of your connections will now be restored to their backed-up state.

3. Re-activate Personal Safe

• Choose: VPN Tracker 365 > Preferences > Personal Safe from the menu bar
• Check your connections, to add them to Personal Safe

Download VPN Tracker free

In some circumstances, VPN Tracker may not be able to store your account login credentials in your Keychain.

To fix this issue, please try the following:

• Quit VPN Tracker
• Open Keychain Access from Applications > Utilities
• Select your login keychain
• Choose File > Lock Keychain “login”
• Then choose File > Unlock Keychain “login”

On newer macOS releases, you may not see the option to lock/unlock your Keychain. In that case, please enter the following command via the Terminal:

security lock-keychain ~/Library/Keychains/login.keychain

security lock-keychain ~/Library/Keychains/login.keychain

Now re-open VPN Tracker and try signing in again.

If the problem still pops up, try this:

• Quit VPN Tracker
• Go back to Keychain Access
• In the search box enter “VPN Tracker User Auth”
• Delete the VPN Tracker User Auth Token entry

Now re-open VPN Tracker and try signing in again.

If none of the tips above work, macOS has an option to reset your Keychain. Note that this should only be tried as a last resort, as it completely resets your login Keychain:

• Open Keychain Access
• Go to Keychain > Preferences
• Choose "Reset Default Keychains…"

If there are any further issues, please contact our support team and include the application logs from this location:
/Library/Application Support/VPN Tracker 365/var/log.

Such a setup is called “Host to Everywhere” in VPN Tracker. All non-local traffic will be sent through the VPN. For this setup to work, it must be properly configured in VPN Tracker and on the VPN gateway:

1. The Network Topology must be set to “Host to Everywhere” in VPN Tracker
2. The VPN gateway must accept an incoming VPN connection with a 0.0.0.0/0 (= everywhere) endpoint

Once these are configured, it should already be possible to establish the VPN connection. However, it is very likely that Internet access will not yet work. For Internet access to work, several more things need to be configured on the VPN gateway:

1. The VPN gateway must route VPN traffic not destined for its local networks out on the Internet
2. This traffic must be subject to Network Address Translation (NAT) in order for replies to reach the VPN gateway
3. In many cases, a suitable remote DNS setup is necessary for DNS resolution to continue to work

Note that not alll VPN gateways can be configured for Host to Everywhere connections. Most devices designed for small office or home networks (e.g. devices by NETGEAR or Linksys) are not capable of dealing with Host to Everywhere connections.

To establish a VPN connection to a certain location (such as your office), you will need a VPN gateway at that location. This gateway could be a hardware VPN gateway device (see our compatibility page for compatible devices and setup guides).

The VPN gateway needs to be connected to the Internet (e.g. to a DSL modem or similar), preferably with a static IP address or it should be capable of using a service like DynDNS.org to map its dynamic IP to a hostname. Configuration is easiest if the VPN gateway is also the router (default gateway) of its network. If the VPN gateway is not the router of its network, a suitable routing setup may be necessary for traffic over the VPN to be routed correctly.

Configuration details can be found in the configuration guides for specific devices.

VPN Tracker 365 fully supports all the latest macOS versions, including macOS Ventura

Starting from macOS 11, Apple have made some key changes to the macOS security architecture. VPN Tracker 365 offers full support for all the latest macOS versions. This includes support for: IPsec VPN, OpenVPN, L2TP VPN, PPTP VPN, SonicWall SSL VPN, Fortinet SSL VPN, Windows SSTP VPN, Cisco AnyConnect VPN and WireGuard® VPN*.

Supported VPN Tracker versions
macOS Ventura requires VPN Tracker 365. Earlier VPN Tracker releases are not supported.

Tip: Sign up for VPN Tracker Insider Updates to get Beta releases as soon as they are available.

*Support for WireGuard®, SSTP, Fortinet SSL, Cisco AnyConnect VPN and PPTP VPN connections under macOS Big Sur and newer are exclusively available in VPN Tracker 365 Pro, VIP, Consultant, Team Member, and Team Member Plus

WireGuard® is a registered trademark of Jason A. Donenefeld.

• Download VPN Tracker for Mac or iPhone
• Copy your VPN connection details from the AnyConnect app
• Connect and enter your username and password when asked

For a certificate to be available in the "Local Certificate" list, it must be present in the Mac OS X Keychain with its corresponding private key.

You can easily check this in the Keychain Access application: If a certificate is listed under "My Certificates" (and not just "Certificates"), its private key is available and you will be able to select it in VPN Tracker as the "Local Certificate".

Important note for CheckPoint VPN users:

The Mac OS X Keychain Access application currently does not understand how to read private keys from some CheckPoint generated certificates.

To properly import the certificate into the Mac OS X Keychain, first convert it using the openssl command line tool:

1. Open a Terminal ("Applications" > "Utilities" > "Terminal")
   
   
2. Convert the certificate to PEM format:

     openssl pkcs12 -in /Users/joe/Desktop/MyCheckPointCert.p12 -out /tmp/out.pem
   

   Replace /Users/joe/Desktop/MyCheckPointCert.p12 with the path to the actual certificate that you want to convert.

   You will first be asked for the password that the certificate is encrypted with. If you do not know it, please ask the administrator who has created your certificate for you. You will then be asked twice for the password that will be used to protect the exported PEM file. You can use the same password that the original certificte was encrypted with. Note that no characters will appear on screen while you type in your passwords. Simply type the password and press the return key.

3. Convert the PEM file back to PKCS#12 (.p12) format:

     openssl pkcs12 -in /tmp/out.pem -export -out ~/Desktop/MyFixedCheckPointCert.p12
   

   Replace /Users/joe/Desktop/MyFixedCheckPointCert.p12 with the path where you want the fixed certificate to be stored.

   You will first be asked for the password that you have just used for exporting to the PEM file, and then for a password to protect the fixed .p12 file with. You can again use the same password for everything.

Now double-click your fixed certificate file to import it into the Mac OS X keychain.

‣Open System Preferences

‣Go to Security

‣Click "Allow"

{S_685}

With both SMB (Windows File Sharing) and AFP (Apple File Sharing), low latency connections are key to achieving good performance. This is of course assuming that you already have a connection with reasonable bandwidth in between the two VPN endpoints (this can be easily verified by transferring a larger file through HTTP or FTP).

Using SSL VPN? Switch to IPSec

In comparison to SSL VPN, IPSec is able to offer much faster connection speeds as it runs on the network layer – level 3 of the OSI – meaning it’s much closer to the physical hardware. This will give you a faster VPN performance.

Learn more in this blog post.

Finder Settings

If you are using the Finder and the issue is mostly with listing folders (but not so much when actually copying files), try turning off icons/icon previews in the Finder's View Options (Cmd-J).

Reducing Latency

If you experience performance issues both when listing folders and when transferring files, your aim should be to reduce latency. Some ways to reduce latency include:

• Avoid high-latency Internet uplinks (e.g. satellite, some types of wireless providers, line aggregation, ...).
• When using a DSL line, see with your ISP if you can get "fast path" enabled (= interleaving turned off). ISPs sometimes market this as an option for online gaming, but it's also very helpful for AFP/SMB or connecting to some types of database backends.
• Make sure VPN traffic is appropriately prioritized in order not to be slowed down by someone else using the same Internet connection.

To measure latency between the two endpoints of the VPN, use ping to a host on the other end of the connection (or, when pinging from the client end, ping the VPN gateway). For your convenience, VPN Tracker has a ping utility built right in, it can be found in the Tools menu.

To measure latency of each endpoint's individual uplink, it's often helpful to do a ping the local router (to make sure there are no unnecessary latencies introduced in the local network) and the ISP's first router (to get an idea if enabling fast path or switching ISPs may be a suitable measure to decrease latency).

If you cannot reduce latency any further:

If you are in a situation where you cannot reduce latency any further (or where the base latency from the distance between the two endpoints itself is so large local measures won't make much difference), consider switching to a file transfer protocol that is less vulnerable to latency, e.g. WebDAV or FTP, or use measures such as reducing the number of files and folders in a hierarchy to increase performance.

1. Start your VPN connection in VPN Tracker
2. Go to the Finder > Go To >Connect to Server
3. In the Server Address field, enter the name or IP address of the server you want to connect to
4. Click on the Connect button.

Create a VPN Shortcut:

This depends on your settings. The most common setup is “Host to Network“, in which case only traffic to the specified remote network(s) will go through the VPN tunnel.

With a “Host to Everywhere” setup, all traffic – except traffic to the local network(s) – goes through the VPN. A Host to Everywhere connection requires a suitable setup on the VPN gateway.

IPsec VPN uses a different protocol (ESP) for the actual data transfer than for establishing the connection (IKE). Since the ESP protocol does not use network ports, NAT (Network Address Translation) routers may have difficulties handling it correctly. Only NAT routers that support "IPSec Passthrough" (sometimes also named "VPN Passthrough" or "ESP Passtrhough") and where this option is also enabled, can handle ESP data packets.

To work around this problem, two alternative tunneling methods exist:

• NAT-Traversal (old, RFC draft version)
• NAT-Traversal (new, RFC standard version)

Which of these methods will work with your connection depends on two properties:

1. Which of these methods allows traffic to pass through your local Internet router.
2. Which of these methods are supported by your VPN remote gateway.

To test for the first property, VPN Tracker will automatically establish three VPN test connections to a VPN gateway hosted by us whenever it detects a new router that has not been tested before. One connection uses plain ESP, the other two either NAT-T method mentioned above. It will remember the test results for this router and take them into account whenever you start a connection from the network location. The reason we are testing with our own gateway is simply that the test requires a gateway supporting all three methods, with a known configuration and a simply way to verify if traffic did arrive at that gateway.

The second property is not tested in advance, VPN Tracker will become aware of that information when it actually tries to connect to your VPN gateway. VPN Tracker will compare the methods your gateway supports with the stored test results. If there is a match, a method that your gateway supports and that was also working during the test, this method will be used. If there is no match, VPN Tracker will immediately stop and show an appropriate error in the log, explaining the situation.

If you suspect a NAT-Traversal issue or you think the previous test results may be wrong or outdated, simply re-run the test:

‣ Make sure NAT-Traversal (Advanced tab) is set to Automatic
‣ Go to "Tools" > "Test VPN Availability"
‣ Click "Test Again"
‣ Wait until the test has completed, then connect to your VPN

The test dialog also allows you to tell VPN Tracker to not test the current location and forget any previously created test results. This is rarely needed and also not recommended but there might be situation where the test results are wrong because access to our VPN gateway is not possible (e.g. it is blocked) and thus the test result are just bogus and say nothing about the true capabilities of your VPN gateway.

There are multiple passwords that VPN Tracker may require: Your admin password for installation, passwords needed for connecting to your VPN or accessing your keychain etc.

This document shows all password prompts you may encounter in VPN Tracker, explains why they are needed and which password should be entered.