self-signed certificate problem since 2.56.1

[name-snrl]

CLI Version

2.56.1

Operating System and Architecture

• macOS (arm64)
• macOS (x86_64)
• Linux (i686)
• Linux (x86_64)
• Linux (armv7)
• Linux (aarch64)
• Windows (i686)
• Windows (x86_64)

Operating System Version

macOS, 26.0, 25A354

Link to reproduction repository

sorry, private one

CLI Command

SENTRY_URL='https://self-hosted.sentry.com/' ./sentry-cli-Darwin-arm64 --auth-token $KEY login --log-level=debug

Exact Reproduction Steps

1. wget https://github.com/getsentry/sentry-cli/releases/download/2.56.1/sentry-cli-Darwin-arm64
2. chmod +x sentry-cli-Darwin-arm64
3. run command above

Expected Results

Everything works fine with the previous version (2.56.0) and with any version on my Linux machine, but on our Mac mini used as a GitHub runner, starting from version 2.56.1, I get the following error:

SSL certificate problem: self-signed certificate in certificate chain

Actual Results

SSL certificate problem: self-signed certificate in certificate chain

Logs

./sentry-cli-Darwin-arm64 --auth-token $KEY login --log-level=debug                         
  INFO    2025-12-25 09:59:17.315643 +04:00 Loaded config from /Users/twl/.sentryclirc
  DEBUG   2025-12-25 09:59:17.316068 +04:00 sentry-cli version: 2.56.1, platform: "darwin", architecture: "arm64"
  INFO    2025-12-25 09:59:17.317005 +04:00 sentry-cli was invoked with the following command line: "./sentry-cli-Darwin-arm64" "--auth-token" "[REDACTED]" "login" "--log-level=debug"
This helps you signing in your sentry-cli with an authentication token.
If you do not yet have a token ready we can bring up a browser for you
to create a token now.

Sentry server: self-hosted.sentry.com
  DEBUG   2025-12-25 09:59:17.317691 +04:00 using token authentication
  DEBUG   2025-12-25 09:59:17.317706 +04:00 retry number 0, max retries: 5
error: API request failed

Caused by:
    0: API request failed
    1: [60] SSL peer certificate or SSH remote key was not OK (SSL certificate problem: self-signed certificate in certificate chainHow is
  INFO    2025-12-25 09:59:17.568053 +04:00 Running update nagger update check
  DEBUG   2025-12-25 09:59:17.568373 +04:00 retry number 0, max retries: 5
  DEBUG   2025-12-25 09:59:17.605368 +04:00 > GET /apps/sentry-cli/latest HTTP/1.1
  DEBUG   2025-12-25 09:59:17.605412 +04:00 > Host: release-registry.services.sentry.io
  DEBUG   2025-12-25 09:59:17.605417 +04:00 > Accept: */*
  DEBUG   2025-12-25 09:59:17.605421 +04:00 > Connection: TE
  DEBUG   2025-12-25 09:59:17.605425 +04:00 > TE: gzip
  DEBUG   2025-12-25 09:59:17.605429 +04:00 > User-Agent: sentry-cli/2.56.1
  DEBUG   2025-12-25 09:59:17.830187 +04:00 < HTTP/1.1 200 OK
  DEBUG   2025-12-25 09:59:17.830255 +04:00 < content-type: application/json
  DEBUG   2025-12-25 09:59:17.830269 +04:00 < Content-Length: 11321
  DEBUG   2025-12-25 09:59:17.830279 +04:00 < access-control-allow-origin: *
  DEBUG   2025-12-25 09:59:17.830289 +04:00 < access-control-allow-headers: sentry-trace, baggage
  DEBUG   2025-12-25 09:59:17.830299 +04:00 < etag: "635db924284d0cb7865cc71950a16d76c0979483"
  DEBUG   2025-12-25 09:59:17.830308 +04:00 < x-from-cache: 1
  DEBUG   2025-12-25 09:59:17.830315 +04:00 < server: granian
  DEBUG   2025-12-25 09:59:17.830323 +04:00 < date: Thu, 25 Dec 2025 05:59:17 GMT
  DEBUG   2025-12-25 09:59:17.830333 +04:00 < Via: 1.1 google
  DEBUG   2025-12-25 09:59:17.830341 +04:00 < Alt-Svc: h3=":443"; ma=2592000,h3-29=":443"; ma=2592000
  INFO    2025-12-25 09:59:17.830460 +04:00 Looking for file named: sentry-cli-Darwin-universal
  DEBUG   2025-12-25 09:59:17.830491 +04:00 body: 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  INFO    2025-12-25 09:59:17.831188 +04:00 Found asset sentry-cli-linux-i686-3.0.1.tgz
  INFO    2025-12-25 09:59:17.831209 +04:00 Found asset sentry-cli-Linux-armv7
  INFO    2025-12-25 09:59:17.831218 +04:00 Found asset sentry-cli-Darwin-x86_64
  INFO    2025-12-25 09:59:17.831225 +04:00 Found asset sentry-cli-linux-arm64-3.0.1.tgz
  INFO    2025-12-25 09:59:17.831232 +04:00 Found asset sentry-cli-win32-i686-3.0.1.tgz
  INFO    2025-12-25 09:59:17.831239 +04:00 Found asset sentry_cli-3.0.1-py3-none-manylinux_2_17_armv7l.manylinux2014_armv7l.musllinux_1_2_armv7l.whl
  INFO    2025-12-25 09:59:17.831246 +04:00 Found asset sentry-cli-Darwin-universal

[linear]

CLI-256

[name-snrl]

oh, yes, our self-hosted version is 25.6.2

[szokeasaurusrex]

Hi @name-snrl, thank you for reaching out, and thank you for your patience with slower than usual response times during the holidays.

I will need some more information about your setup to be able to help you here:

1. How did you configure the self-signed certificate to be trusted on the Mac mini? (Keychain? Environment variable? Some other method?)
2. Are you using any corporate proxy or SSL inspection?
3. If you downgrade to Sentry CLI version 2.56.0 on the same Mac mini, without changing anything else in the environment, does the CLI work again? If not, maybe some other environment change is causing the problem.

[name-snrl]

How did you configure the self-signed certificate to be trusted on the Mac mini? (Keychain? Environment variable? Some other method?)

Keychain. Following command: sudo security add-trusted-cert -d -r trustRoot -k /Library/Keychains/System.keychain /path/to/file.crt

Are you using any corporate proxy or SSL inspection?

No

If you downgrade to Sentry CLI version 2.56.0 on the same Mac mini, without changing anything else in the environment, does the CLI work again? If not, maybe some other environment change is causing the problem.

Yes. I bisected many versions simply wget them and run (in the same env) as explained in initial message