Connection to Azure Data Studio and Heroku just failed.

Question

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 770 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This would explain why both Heroku and Azure Data Studio are affected simultaneously—both may be using outdated or misconfigured SSL settings.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 770 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

Hope this helps. Do let us know if you any further queries.
Prasad Chaganti 770 Reputation points Microsoft External Staff Moderator

2025-05-12T21:37:01.1833333+00:00

Hi ckcDevelopment Admin,

We haven’t heard from you on the last response and was just checking back to see if you have a resolution yet. In case if you have any resolution please do share that same with the community as it can be helpful to others. Otherwise, will respond with more details and we will try to help.
Prasad Chaganti 770 Reputation points Microsoft External Staff Moderator

2025-05-13T21:47:59.0133333+00:00

Hi ckcDevelopment Admin,

We haven’t heard from you on the last response and was just checking back to see if you have a resolution yet. In case if you have any resolution, please do share that same with the community as it can be helpful to others. Otherwise, will respond with more details and we will try to help.
Mihir Saxena 0 Reputation points Microsoft External Staff Moderator

2025-05-15T05:18:55.63+00:00

Hi @ckcDevelopment Admin
We haven’t heard from you on the last response and was just checking back to see if you have a resolution yet. In case if you have any resolution, please do share that same with the community as it can be helpful to others. Otherwise, will respond with more details and we will try to help.
Mihir Saxena 0 Reputation points Microsoft External Staff Moderator

2025-05-16T10:31:16.74+00:00

Hi @ckcDevelopment Admin We haven’t heard from you on the last response and am just checking back to see if you have a resolution yet. In case if you have any resolution, please do share that same with the community as it can be helpful to others. Otherwise, will respond with more details and we will try to help.

1 answer

Your answer

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 770 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 770 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

Hope this helps. Do let us know if you any further queries.
Prasad Chaganti 770 Reputation points Microsoft External Staff Moderator

2025-05-12T21:37:01.1833333+00:00

Hi ckcDevelopment Admin,

We haven’t heard from you on the last response and was just checking back to see if you have a resolution yet. In case if you have any resolution please do share that same with the community as it can be helpful to others. Otherwise, will respond with more details and we will try to help.
Prasad Chaganti 770 Reputation points Microsoft External Staff Moderator

2025-05-13T21:47:59.0133333+00:00

Hi ckcDevelopment Admin,

We haven’t heard from you on the last response and was just checking back to see if you have a resolution yet. In case if you have any resolution, please do share that same with the community as it can be helpful to others. Otherwise, will respond with more details and we will try to help.
Mihir Saxena 0 Reputation points Microsoft External Staff Moderator

2025-05-15T05:18:55.63+00:00

Hi @ckcDevelopment Admin
We haven’t heard from you on the last response and was just checking back to see if you have a resolution yet. In case if you have any resolution, please do share that same with the community as it can be helpful to others. Otherwise, will respond with more details and we will try to help.
Mihir Saxena 0 Reputation points Microsoft External Staff Moderator

2025-05-16T10:31:16.74+00:00

Hi @ckcDevelopment Admin We haven’t heard from you on the last response and am just checking back to see if you have a resolution yet. In case if you have any resolution, please do share that same with the community as it can be helpful to others. Otherwise, will respond with more details and we will try to help.

Answer 1

Hi @ckcDevelopment Admin

The error that you're facing "invalid authorization specification" might be because of the fact that Azure Database for PostgreSQL requires SSL connections by default. If the client (Heroku app or Azure Data Studio) is not explicitly configured to use SSL, the server will reject the connection even if the credentials are correct.

Kindly follow the mentioned steps to troubleshoot the error:

Confirm SSL is required by your Azure PostgreSQL server:

Go to "Connection Security" in your Azure Database for PostgreSQL
Ensure that “Enforce SSL connection” is enabled.

Update the DATABASE_URL with SSL mode:

If your connection string doesn’t include SSL settings, update it to:

postgres://username:******@yourserver.postgres.database.azure.com:5432/dbname?sslmode=require

For Heroku:

heroku config:set DATABASE_URL="postgres://username:******@yourserver.postgres.database.azure.com:5432/dbname?sslmode=require"

Configure Azure Data Studio to use SSL:

If you’re connecting using Azure Data Studio, make a "New Connection"

Enter your connection details (Server name, Username, Password and DB name)
Click "Advanced" tab
Set sslmode: require

If your app requires strict SSL validation, you may need to add a root certificate.

Download the official Azure CA certificate from:

https://learn.microsoft.com/en-us/azure/postgresql/concepts-ssl-connection-security#ca-certificate

Kindly verify the same at your end. Hope it helps. Kindly accept the answer by clicking on Accept answer button. Thankyou

Share via

Connection to Azure Data Studio and Heroku just failed.

1 answer

Your answer