Retry Docker SSI Agent install

[nccatoni]

Motivation

Docker SSI image builds occasionally fail when transient connectivity errors interrupt the Datadog Agent installer. Retrying only the installer-script download does not recover failures that occur while the downloaded installer is running, and continuing after such a failure obscures the root cause.

Changes

• Retry the Datadog Agent installer up to three times, with a short delay between attempts, in both Docker SSI installation paths.
• Centralize retry attempts, delays, logging, and terminal failure handling in one generic helper; the download helper wraps it while preserving its five-attempt behavior.
• Explicitly abort both SSI installation scripts after the final failed Agent installer attempt, ensuring the Docker build stops before cleanup or later steps can mask the failure.

Testing

• Verified with synthetic shell commands that a transient installer failure succeeds on the third attempt and persistent failures return non-zero after exactly three attempts.
• Verified that both complete SSI scripts exit with status 1 after exhausted retries and that the standard path does not execute Agent cleanup afterward.
• Verified that the download wrapper delegates five attempts with the expected URL and output filename.
• Passed Bash syntax checks, ShellCheck, and git diff --check for all changed scripts.

Workflow

1. ⚠️ Create your PR as draft ⚠️
2. Work on you PR until the CI passes
3. Mark it as ready for review
   • Test logic is modified? -> Get a review from RFC owner.
   • Framework is modified, or non obvious usage of it -> get a review from R&P team

🚀 Once your PR is reviewed and the CI green, you can merge it!

🛟 #apm-shared-testing 🛟

Reviewer checklist

• Anything but tests/ or manifests/ is modified ? I have the approval from R&P team
• A docker base image is modified?
  • the relevant build-XXX-image label is present
• A scenario is added, removed or renamed?
  • Get a review from R&P team

---

PR by Bits - View session in Datadog

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[datadog-prod-us1-3]

View session in Datadog

Bits Code status: ✅ Done

Comment @DataDog to request changes

[datadog-datadog-prod-us1]

I can only run on private repositories.

[github-actions]

CODEOWNERS have been resolved as:

utils/build/ssi/base/download_with_retry.sh                             @DataDog/system-tests-core
utils/build/ssi/base/install_script_ssi.sh                              @DataDog/system-tests-core
utils/build/ssi/base/install_script_ssi_installer.sh                    @DataDog/system-tests-core

[datadog-prod-us1-3]

✅ All CI checks and tests passed.

🎉 All green!

🧪 All tests passed
❄️ No new flaky tests detected

_{This comment will be updated automatically if new data arrives.
🔗 Commit SHA: d012eeb | Docs | View more details | Give us feedback!}

[chatgpt-codex-connector]

Codex Review Summary

This comment shows the latest Codex review activity on this pull request.

Review	Status	Commit	Review trigger
📝 Code Review	✅ Completed 2026-09-14T13:47:58.249782Z	d012eeb	Draft marked ready

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