[Bug] OTel not initializing on Windows Desktop despite correct remote-settings.json cache

Preflight Checklist

• [x] I have searched existing issues and this hasn't been reported yet
• [x] This is a single bug report (please file separate reports for different bugs)
• [x] I am using the latest version of Claude Code

What's Wrong?

OTel is not initializing at all on my machine despite correct managed settings configuration.
Zero OTel logs appear in main.log, and Datadog shows 0 entries for my email.

Evidence:

• ~/.claude/remote-settings.json contains all correct OTel vars under "env" key:

CLAUDE_CODE_ENABLE_TELEMETRY=1, OTEL_LOGS_EXPORTER=otlp, OTEL_EXPORTER_OTLP_* etc.

• main.log shows [remoteManagedSettings] fetched (3 keys) on every startup
• No OTel initialization logs in main.log (searched: otel, OTEL, telemetry) — zero matches
• Datadog: 0 logs for service:claude-code filtered by my email across all restarts

What Should Happen?

OTel should initialize and send logs/metrics to Datadog as it does for other team members
on the same Team Plan with the same managed settings (2,480 entries confirmed for others).

Error Messages/Logs

# main.log - OTel/telemetry related entries (zero matches)
# Searched for: otel, OTEL, telemetry → 0 results

# Only relevant startup logs found:
2026-06-11 11:52:26 [info] [startup-perf] { ... }
2026-06-11 11:52:27 [info] [remoteManagedSettings] fetched (3 keys)

# No OTel initialization logs at all across multiple restarts

Steps to Reproduce

1. Configure OTel env vars via Team Plan managed settings in admin console:

• CLAUDE_CODE_ENABLE_TELEMETRY=1
• OTEL_LOGS_EXPORTER=otlp
• OTEL_EXPORTER_OTLP_LOGS_ENDPOINT=https://otlp.datadoghq.com/v1/logs
• (and other OTEL_EXPORTER_OTLP_* vars)

1. Confirm ~/.claude/remote-settings.json contains all vars correctly
2. Fully restart Claude Code Desktop on Windows 11
3. Check main.log for OTel initialization logs → zero matches
4. Check Datadog for logs → 0 entries

Claude Model

None

Is this a regression?

I don't know

Last Working Version

_No response_

Claude Code Version

2.1.172

Platform

Anthropic API

Operating System

Windows

Terminal/Shell

PowerShell

Additional Information

Key finding: remote-settings.json contains all correct OTel env vars,
but OTel initialization appears to happen before the file is read.

Other team members on same Team Plan successfully send logs to Datadog.
Only this Windows machine produces zero OTel logs.

Hypothesis: OTel initializes in Electron main process before
remote-settings.json is applied — Windows-specific timing bug.