Unable to establish a secure connection to the Gemini API from VAST Smalltalk (AI Assistant)

[hiddenagendageek]

🏷️ Discussion Type

Bug

Body

Hi everyone,

Good day.

I'm currently trying to integrate the Gemini API with VAST Smalltalk for "AI Assistant", but I'm running into an issue when attempting to retrieve the available models.

When I click Refresh in the provider configuration, I receive the following error:

Failed to establish secure connection to https://generativelanguage.googleapis.com/

I've attached a screenshot of the error.

I'm trying to determine whether this is related to:

TLS/SSL support in VAST Smalltalk
HTTP client configuration
Certificate validation or missing CA certificates
Proxy or firewall settings
Or if the Gemini API requires something that VAST's HTTP client doesn't currently support

Has anyone successfully connected to the Gemini API (or another HTTPS REST API with similar security requirements) from VAST Smalltalk?

I'd appreciate any suggestions on:

What I should check first.
Whether additional TLS or certificate configuration is required.
Any examples of connecting to modern HTTPS APIs from VAST.

Thanks in advance for any advice!

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[kaungzawhein543]

Hi there,

This error usually means the TLS handshake is failing before the request even reaches Google. Here are the three most likely culprits to check in VAST Smalltalk:

1. Missing CA Certificates (Most Common): The HTTP client needs to verify Google's SSL certificate chain. If VAST isn't configured to point to an up-to-date local root certificate bundle (like a cacert.pem), the connection drops instantly.
2. Outdated TLS/OpenSSL Version: Gemini requires TLS 1.2 or TLS 1.3 and modern cipher suites. If your VAST runtime is bound to an older version of OpenSSL (like 1.0.x), it won't be able to negotiate a secure connection with Google's servers.
3. How to test it: See if you can temporarily turn off certificate verification (set something like verifyPeer: false) in your VAST configuration. If the "Refresh" button works with verification disabled, you just need to link your root certificates properly.

Give the certificate path a check first—that usually fixes it!

[Syaptiyan]

This looks like an SSL/TLS certificate issue. Here are some things to try:

1. Update your certificates:

sudo apt update && sudo apt install ca-certificates

2. Check if the Gemini API endpoint is accessible:

curl -v https://generativelanguage.googleapis.com/

3. Set SSL_CERT_FILE environment variable:

export SSL_CERT_FILE=/etc/ssl/certs/ca-certificates.crt

4. If behind a proxy/firewall - Make sure the firewall allows outbound HTTPS connections to googleapis.com

5. Try using HTTP instead of HTTPS temporarily to confirm if it is an SSL issue (not recommended for production)

The error usually means the client cannot verify the server certificate. Updating CA certificates fixes it in most cases.