Asa Vpn Certificate

The video gets you started on SSL VPN on Cisco ASA with certificate installation. You will learn how to generate a Certificate Signing Request (CSR) on the ASA, submit it to your Certificate Authority (CA), and import the signed certificate back to the ASA. This tutorial is to show you how to install a HTTPS/SSL certificate on an ASA. This is often used when WebVPN or AnyConnect is configured which uses SSL. Without a certificate installed the users is given warnings and errors about a missing or invalid certificate. The SSL VPN connection is established between a Cisco IP phone and a Virtual Private Network (VPN) head-end. The VPN head-end can be a Cisco Adaptive Secure Appliance (ASA) or Datagram Transport Layer Security (DTLS) enabled on a Cisco IOS SSL VPN router. The encrypted traffic consists of voice and signaling. SSL Certificate Installation for Cisco ASA 5500 VPN. How to generate a CSR in Cisco ASA 5500 SSL VPN/Firewall From the Cisco Adaptive Security Device Manager (ASDM), select 'Configuration' and then 'Device Management.' Expand 'Certificate Management,' then select 'Identity Certificates,'.

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If you are facing “Cisco AnyConnect Certificate Validation Failure” problem while trying to connect on the AnyConnect Client, then you are in right place. Here, we are discussing on “How to fix AnyConnect Certificate error” in details and providing some recommended methods to fix this error. Let’s starts the discussion.

What is Cisco AnyConnect?

Cisco AnyConnect” is proprietary application that lets users connect to VPN service. Many universities use this application as part of service they pay for from Cisco that’s why public institutions unnecessarily rely on this closed-source software for their own students. This doesn’t just amount to handling control to a private corporation, thereby privatizing public money. This software also provide extra security layer to reduce potentially unwanted attacks and privacy vulnerability.

Cisco AnyConnect is unified endpoint agent that delivers multiple security services to protect the enterprise. Its wide range of security services includes functions such as remote access, posture enforcement, web security features, and roaming protection. It gives all the security features for IT department to provide a robust, user-friendly, and highly secure mobile experience as well.

Cisco AnyConnect security mobility client is modular endpoint software product that not only provides VPN access via SSL (Secure Socket Layer) and IPsec IKEv2 but also offers improved security via various built-in modules including compliance through VPN and ASA or through wired /wireless, and VPN with Cisco identity Services Engine (ISE), Off-network roaming protection with Cisco Umbrella.

Since, Cisco has been a long-term target of NSA spying program. It also doesn’t work well on Linux. There is nothing wrong with supporting free and open source solutions like OpenVPN which are used by numerous users worldwide. Linux, iOS, Windows, MacOS and Android OS are some of the popular tools that integrate with Cisco Anyconnect.

Cisco AnyConnect Review: Features

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  • Mobile Device Support: AnyConnect services can be delayed on most popular devices used by today’s diverse workforce. Administrators need to support end-user productivity by providing personal mobile devices with remote access to the computer network.
  • Off-Network Protection (DNS Layer Security): Cisco AnyConnect protects devices when they are off the corporate network. The Umbrella roaming enforces security at DNS layer to protect against malware, phishing and Command -and-Control callbacks over any protocol whether you turn Off the VPN or forgot to turn it on.
  • Web security: Cisco AnyConnect has in-built web security feature based on cloud web security. Combining web security with VPN access, administrators can provide comprehensive, high security mobility to all end users.
  • Network Visibility: Cisco AnyConnect network visibility module on MacOS, Windows OS, Linux and Samsung Knox-enabled devices gives administrators the ability to monitor endpoint application usage to uncover potential behavior anomalies and to make more informed network designed decisions.

What is “Cisco AnyConnect Certificate Validation Failure” Error on Windows?

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“AnyConnect Certificate error” is common error reported by numerous users on Cisco official forum site or other popular platforms and asked for the solution. Users explained on Cisco Community website that the error appears when they run their own CA that gives out the client certificates for our users as well as the identity certificate for ASA, and in order to click on “Connect” on AnyConnect Client, their client receives “No Valid Certificates available for authentication” message.


Furthermore, he also created a DART bundle and in there I can see that the certificate is selected from the “Microsoft Store”, but after that he receive several errors regarding SCHANNEL. Then, he tried another certificate authentication and finds no certificates followed by “Cisco AnyConnect Certificate Validation Failure” Error.

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Certificate Validation Failure Error States:

When we talk about “Anyconect Certificate validation Failure error”, it explained that it can’t verify the VPN server which is to be expected since it uses the self-signed certificate, but if they connect anyway, then they receive the certification selection and the login works fine. It means username & password for login is taken from the certificate.

[Tips & Tricks] How to fix Cisco AnyConnect Certificate Validation Failure Problem?

Procedure 1: Repair the Installation

Step 1: Click on “Start” button and type “Control Panel” in Windows search and open “Control Panel”

Step 2: In the opened “Control Panel”, choose “Uninstall a program” and find “Cisco AnyConnect VPN” client and choose “Repair”

Step 3: Follow On-Screen instructions to finish the repairing process. Once done, restart your computer and please check if the problem is resolved.

Procedure 2: Allow VPN to freely communicate through Firewall

Step 1: Click on “Start” button and type “Allow an App” in Windows Search and open “Allow an App through Windows Firewall”

Step 2: Now, click on “Change Settings”

Step 3: Make sure that “Cisco VPN” is on the list and it’s allowed to communicate through Windows Firewall. If not, click “Allow another App” and add it

Step 4: Check both “Private” and “Publicrong” > Network boxes

Step 5: Confirm changes and open Cisco VPN

Procedure 3: Check Virtual Adapter driver in Device Manger and update it

Step 1: Press “Windows + X” key from keyboard and select “Device Manager”

Step 2: In the opened “Device Manager” window, locate and expand “Network Adapters”

Step 3: Right-click on Virtual Adapter and select “Update driver software”

Step 4: Follow On-Screen instructions to finish the updating process.

Step 5: Once done, restart your computer and please check if the problem is resolved.

Asa Vpn Certificate

Procedure 4: Tweak Registry and Repair Cisco VPN

Step 1: Press “Windows + R” keys together from keyboard and type “regedit” in “Run Dialog Box” and then hit “Ok” button

Step 2: In the opened “Registry Editor” window, navigate to “HKEY_LOCAL_MACHINE/SYSTEM/Current/Control/SetServices/CVirtA

Step 3: Right-click on the “DisplayName” registry entry and choose “Modify”

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Step 4: Under “Value Data” section, make sure that the only body of text which stands is Cisco System VPN Adapter

Step 5: Save the changes and try running Cisco AnyConnect VPN again.


Procedure 5: Update the AnyConnect

Step 1: Go to “ASDM > Configuration > Remote Access VPN > Network (Client) Access > AnyConnect Client Software”

Step 2: You can either replace the existing the image or add a new one.

Step 3: After that, connect to the ASA. The client will be updated automatically.

Procedure 6: Create Trustpoints for each certificate being installed

Step 1: Open the “Cisco ASDM”

Step 2: Under “Remote Access VPN” window pane, click on “Configuration” tab and expand “Certificate Management” and click on “CA Certificates”

Step 3: Click on “Add” button

Step 4: Assign a “TrustPoint Name” to the certificate like “DigiCertCA2” and select “Install from the file” Radio button and browse to “DigiCertCA2.crt”, then click on “Install Certificate”. Repeat this process of adding new trustpoint and installing certificate file for “DigiCertCA.crt”

Step 5: Under “Remote Access VPN”, expand “Certificate Management” to “Identify Certificates”. Select the identity you created for the CSR with “Expiry Data” and click on “Install > Install Certificate”

Step 6: The Certificate now needs to be enabled. To do so, click on “Advanced > SSL Settings > Edit > Primary Enrolled Certificate” and select your certificate and then click on “Ok”

Step 7: ASDM will then show your Certificate details under trustpoint

Procedure 7: Perform Clean Reinstallation

Step 1: Navigate to “Control Panel” and choose “Uninstall a program”

Step 2: Uninstall “Cisco AnyConnect VPN Client”

Step 3: Navigate to System partition and delete everything Cisco-related from programs folder

Step 4: Once uninstalled completely, restart your computer

Step 5: After that, download latest version of “Cisco AnyConnect” from “Cisco official website”

Step 6: Double-click on installer file and follow on-screen instructions to finish the installation.

Step 7: Once installed, restart your computer again and please check if the AnyConnect Certificate error is resolved.


Cisco AnyConnect is VPN service that offers Standard VPN encryption and protection. When we talk about AnyConnect Secure Mobility Client, it is modular endpoint software product. It not only provides Virtual Private Network (VPN) access through Secure Sockets layer (SSL) and Internet Protocol Security (IPsec) Internet Key Exchange version2 (IKEv2), but also offers enhanced security through various built-in modules.

I am sure this article helped you to “Fix Cisco AnyConnect Certificate Validation Failure Windows 10” with several easy methods/procedures. You can choose/follow either one or all procedures to fix this issue.

If you are unable to fix Cisco AnyConnect Certificate Validation Failure problem with the solutions mentioned above, then it might possible that your System has infected with malware or viruses. According to security researchers, malware or viruses cause several damages in your computer.

In this case, you can scan your computer with powerful antivirus software that has the ability to delete all types of malware or viruses from System.

In order to not get the annoying “Invalid certificate” errors in Internet Explorer we need to purchase and install a third party certificate for the ASA. Then we can associate the WebVPN with the certificate so we don’t get the warnings. Of course, you can do this through the ASDM, but what fun is that? CLI all the way, here we go.

-Insert your relevant information between <>
-Console prompts are show in green
-Text in blueare variable names I made up, feel free to change them
-Note sections are in italics and embedded directly within the code below
-During the install/setup the CLI asks several questions. I note when they will appear by inserting a line beginning with ‘Question Prompt –‘ in between the lines of code. I also put the response you should enter after the line in bold.

Verify that your clock is set correctly
To do this, issue the ‘show clock’ command at the CLI. If it isn’t configured correctly, define a NTP server (Which you should have done during initial config) and ensure your time zone is set correctly. I usually use as an NTP server. You can resolve it to an IP to get rid of the DNS lookup.

Generate the CSR
ASA(config)# crypto key generate rsa label <Your domain name> modulus 2048
Notes: I use the domain name that I am going to use for the label name, it just makes it easier if everything is the same (FQDN, System FQDN, Label, etc….). An example would be ‘’. Additionally I use a 2048 bit modulus because GoDaddy (The third party CA I am using) will no longer accept the 1024 bit modulus.
ASA(config)# crypto ca trustpoint <Your domain name>
ASA(config-ca-trustpoint)# subject-name CN=<Your domain name>, OU=<Organization Unit>, O=<Organization Name>, C=<Country (US)>, St=<Your State>, L=<Your City>
ASA(config-ca-trustpoint)# keypair <Your domain name>
ASA(config-ca-trustpoint)# fqdn <Your domain name>
ASA(config-ca-trustpoint)# enrollment terminal
ASA(config-ca-trustpoint)# exit
ASA(config)# crypto ca enroll <Your domain name>
Question Prompt – Include the device serial number in the subject name? [yes/no]:NO
Question Prompt – Display Certificate Request to terminal? [yes/no]:YES
Notes: After answering YES the CLI will output the CSR. You need to copy the CSR so you can submit it to your Certificate Authority (GoDaddy in this case)
Redisplay enrollment request? [yes/no]:NO

Submit your CSR to your Certificate Authority
Again, I used GoDaddy because it seemed to be the cheapest. The certificate was less then $30 for the year. You purchase a certificate credit and then when you are ready to submit your CSR you go into their Certificate Management Portal under your login and submit the CSR. After submitting the request it took about 5 minutes for my certificate to be generated. You download the certificate file in Zip format. In the Zip file you should have two certificates. One is the certificate for the FQDN which you purchased and the other is the certificate for the CA. This is where it gets a little tricky. First you need to authenticate the CA by importing their certificate. Then you need to import your actual certificate. I’m not going to get into the details of how certificates work but if you don’t know how, you should find out. Google ‘Public Key encryption’. Alright, so my Zip file had two certificates in it.

gd_bundle.crt – The certificate for the CA
<Domain name>.crt – The certificate for my domain

You’ll need to export both of the certificates to Base-64 encoded X.509. To do this in Windows double click the certificate. A certificate window with three tabs should appear as shown below.

Click on the second tab ‘Details’ and select the ‘Copy to File…” button

This will open the Certificate Export Wizard. Press NEXT

On the next screen select ‘Base-64 encoded X.509 (.CER)’ and press NEXT

On the following screen select a location to output the file to and press NEXT

Press FINISH on the summary screen. You should get a pop up window indicating that export was successful.

Now browse to where you chose to store the certificate, right click on it, select ‘Open With’, and choose WordPad. When you open it in WordPad you should get something similar to what is shown below.

Perform this certificate Export for your certificate as well as the CA’s certificate. During the rest of the walk through I will refer to these exports as “CA Certificate”(The CA’s certificate) and “CA Certificate Response”(The certificate for your domain).

Install the certificates on the ASA
ASA(config)# crypto ca authenticate <Your domain name>
Notes: You will now receive the prompt shown below.
”Enter the base 64 encoded CA certificate. End with the word 'quit' on a line by itself”
Copy the CA Certificate and paste it into the CLI window. Then make sure you are on a new line, type to the word quit, and press enter.

Question Prompt – Do you accept this certificate? [yes/no]:yes
Notes: After you accept the certificate you should get a message indicating that the certificate import was successful
ASA(config)# exit
ASA(config)# crypto ca import <Your domain name> certificate
Notes: You will now receive the prompt shown below.
”Enter the base 64 encoded CA certificate. End with the word 'quit' on a line by itself”
Copy the CA Certificate Response and paste it into the CLI window. Then make sure you are on a new line, type to the word quit, and press enter. After you press enter you should get a message indicating that the certificate import was successful

Cisco Asa Vpn Certificate Validation Failure

Tell WebVPN to use your new certificate
ASA(config)# ssl trust-point <Your domain name> outside

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You can use the command ‘show crypto ca certificates’ to verify that your certificates imported successfully. Of course the other way to test would be to just connect to the outside IP on SSL and see if you still get that annoying warning.