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Cannot confirm it is connected to secure gateway

I've just upgraded to Mac OS High Sierra, and I'm starting to receive the error:

 

AnyConnect cannot confirm it is connected to your secure gateway.  The local network may not be trustworthy.  Please try another network.

 

I'm using version 4.5.02033

 

 

5 Replies 5

redbob_six
Level 1
Level 1
updated the certificate / Trustpoint on our ASA 5510 with SHA256 pkcs 'bag' and this solved the issue.

This was helpful:
https://supportforums.cisco.com/t5/security-documents/install-a-pkcs-ssl-certificate-in-asa-using-cli/ta-p/3163832

Using apple version 4.5.02033, but this works with multiple older versions of AnyConnect

Could you please explain the steps (in more detail) which need to be performed to solve the problem? How do I update a trustpoint on ASA5510 with a MAC?

Hi Nilorac,

The notes on the link I prevously posted are helpful, I just followed those. When you say from a MAC, to be clear I also used a MAC but used CLI and NOT ASDM. There are possibly multiple ways to achieve this but this is what I did.

Create a base 64 encoded pkcs12 certificate file.

On the ASA5510:
Confirm what trust point certificates already exist on the device:
MAIN_ASA(config)# show crypto ca trustpoints
Expect to see something like this, there could be more than one:
Trustpoint {your cert name EG]:bob.net
    Subject Name:
    cn=GlobalSign Organization Validation CA - G2
    o=GlobalSign nv-sa
    c=BE
          Serial Number: [unique certificate number here]
    Certificate configured.

As a backup export the current certificate(s) out to a pkcs12 file format:
MAIN_ASA(config)# crypto ca export bob.net pkcs12 {create a long password}
copy the output to a file and also save the password with it

Import a new certificate:
MAIN_ASA(config)# crypto ca import bob.net-sha256 pkcs12 printer

Paste the contents of the base 64 encoded pkcs12 file you have already created. 
Ensure the contents have a BEGIN and an a END statement
THEN
After pasting, on a new line End with the word "quit"
See below
-----BEGIN PKCS12-----


MIIGDj****************************************************wFADCB


....
....

....
....


MIIGDj****************************************************wFADCB


-----END PKCS12-----


quit
INFO: Import PKCS12 operation completed successfully


Prove the new trust point cert has been imported corrected:
MAIN_ASA(config)# show crypto ca trustpoints

Expecting to see both:

Trustpoint bob.net
    Subject Name:
    cn=GlobalSign Organization Validation CA - G2
    o=GlobalSign nv-sa
    c=BE
          Serial Number: [unique certificate number here]
    Certificate configured.


Trustpoint bob.net-sha256:
    Subject Name:
    cn=GlobalSign Organization Validation CA - SHA256 - G2
    o=GlobalSign nv-sa
    c=BE
          Serial Number: [unique certificate number here]
    Certificate configured.

I then disabled requests pointing at the OLD  certificate as we no longer needed this
MAIN_ASA(config)# no ssl trust-point bob.net

Point SSL requests at the new certificate
MAIN_ASA(config)# ssl trust-point bob.net-sha256

Confirm this has worked:
show run | i trust-point

 

NB without knowing what setup, version, configuration you have running I have no control over the inpact of reapeating the above will have on your device, you do this at your own risk.

HolgerHelmut
Level 1
Level 1

Anyconnect 4.5 stopped working every since I upgraded to high sierra 10.13.4 today. It give me the "

AnyConnect cannot confirm it is connected to your secure gateway.  The local network may not be trustworthy.  Please try another network." message.

 

It worked before the upgrade and works on a laptop that has sierra 10.13.3 on it. Any ideas?

I have the same issue, I wish I hadn't updated now, because I can't find an easy solution.  Importing a certificate would easy enough with the instructions above, except the part where it says create a new base64 certficate.  I think it would be easier just to buy one from namecheap, unless the OP can show where he created the new cert for us maybe?