Connection to Azure Data Studio and Heroku just failed.

ckcDevelopment Admin 0

Cannot connect to Azure Data Studio or Heroku anymore. I changed nothing and it just happened out of no where. I can connect to the server just fine in the Azure home page.

Failed connections due to invalid authorization specification.

ckcDevelopment Admin 0 Reputation points

2025-05-09T16:22:45.07+00:00

I can connect to the server just fine in the Azure home page.
Prasad Chaganti 645 Reputation points Microsoft External Staff Moderator

2025-05-09T19:29:57.31+00:00
Hi ckcDevelopment Admin,

The issue you're facing sudden failed connections to Azure Data Studio and Heroku with an "invalid authorization specification" error is likely caused by SSL/TLS configuration mismatches or token cache issues, especially if no changes were made on your end.

Root Causes:

1.SSL/TLS Mismatch

The PostgreSQL server enforces TLS 1.2+, and

The client (Azure Data Studio or Heroku CLI) attempts to connect using TLS 1.0 or 1.1, which are now blocked.

This would explain why both Heroku and Azure Data Studio are affected simultaneously—both may be using outdated or misconfigured SSL settings.

2.Azure Token Cache Corruption

If you're using Azure Active Directory (AAD) authentication in Azure Data Studio, a corrupted or stale token cache can also cause this error

Please follow the below steps:

For Azure Data Studio:

1.Clear Azure Token Cache:

Open the Command Palette (Ctrl+Shift+P)

Run: Clear Azure Token Cache

Restart Azure Data Studio and try reconnecting.

2.Check Connection Settings:

Ensure SSL mode is set to require or verify-full depending on your server’s configuration.

If using AAD, ensure your credentials are refreshed.

For Heroku:

1.Update SSL Settings:

In your DATABASE_URL, ensure the SSL mode is set to require:

?sslmode=require

You can update this via the Heroku CLI or dashboard.

2.Check Heroku Postgres Logs:

Run: heroku logs --tail --app <your-app-name>

Look for SSL or authentication-related errors.

if the Issue Persists

Try connecting via psql or another client to isolate whether the issue is client-specific.

Enable verbose logging in Azure Data Studio to capture more details.

I hope this information helps. Please do let us know if you have any further queries.
ckcDevelopment Admin 0 Reputation points

2025-05-09T20:20:36.43+00:00

Hello. Thank you for that. My question for Heroku is, I am using their postgreSQL app that connects to the Azure DB. How can I require SSL if the DATABASE_URL is set to that postgreSQL application key?
Prasad Chaganti 645 Reputation points Microsoft External Staff Moderator

2025-05-10T00:26:56.8066667+00:00
Hi ckcDevelopment Admin,

Thanks for the response.

When using Heroku’s PostgreSQL add-on to connect to an Azure-hosted PostgreSQL database, and your DATABASE_URL is managed by Heroku, you can still enforce SSL by modifying the connection string or setting environment variables.

1: Append ?sslmode=require to the DATABASE_URL

If your DATABASE_URL looks like this:

postgres://username:password@host:port/dbname

Update it to:

postgres://username:password@host:port/dbname?sslmode=require

You can do this in Heroku by running:

heroku config:set DATABASE_URL="postgres://username:password@host:port/dbname?sslmode=require" --app your-app-name

Note: If Heroku auto-generates the DATABASE_URL (e.g., from an add-on), you may need to create a custom config var like AZURE_DB_URL and use that in your app instead.

2: Use a Custom Environment Variable

Leave DATABASE_URL as-is.

Create a new config var:

heroku config:set AZURE_DB_URL="postgres://...your-azure-db...?sslmode=require"

Update your app’s database connection logic to use AZURE_DB_URL instead of DATABASE_URL.

3: Use a .pg_service.conf File (Advanced)

If your app uses libpq or a PostgreSQL client that supports service files, you can define SSL settings in a .pg_service.conf file and reference it via the PGSERVICE environment variable.

Please do let us know if you have any further queries.

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