Python Logging Best Practices

Self-Evolving Skill: This skill improves through use. If instructions are wrong, parameters drifted, or a workaround was needed — fix this file immediately, don't defer. Only update for real, reproducible issues.

When to Use This Skill

Use this skill when:

• Setting up Python logging for any service or script
• Configuring structured JSONL logging for analysis
• Implementing log rotation
• Choosing between lightweight (zero-dep) and full-featured logging
• Adding logging to containerized, systemd, or local applications

Overview

Unified reference for Python logging patterns optimized for machine readability (Claude Code analysis) and operational reliability. Starts with the lightest viable approach and scales up only when needed.

Decision Heuristic: Start Light, Scale Up

Is it < 5 services on a single machine, < 1 event/sec?
  YES → Lightweight Pattern (print + JSONL telemetry)
  NO  → Is it containerized / serverless?
    YES → stdout JSON (any library), no file rotation
    NO  → Is OTel tracing required?
      YES → structlog + OTel
      NO  → loguru (CLI tools) or stdlib RotatingFileHandler

Preferred: Lightweight Pattern (Zero Dependencies)

For: < 5 systemd services, single server, single operator. Battle-tested in production by ccmax-monitor.

This pattern uses a two-channel architecture:

• Channel 1: print(flush=True) → systemd journald (operational logs, human-readable)
• Channel 2: Append-only JSONL file (structured telemetry, machine-readable)

This maps to the 12-Factor App's "treat logs as event streams" principle. journald handles ops (rotation, filtering, metadata), while the JSONL file serves domain telemetry for post-mortem analysis.

Architecture: Three-Concern Separation

Complete Lightweight Example

"""Append-only JSONL telemetry logger with size-based rotation.

Zero external dependencies. Works with systemd journald for ops logging
and a separate JSONL file for structured machine-readable telemetry.
"""

import json
from datetime import datetime, timezone
from pathlib import Path

TELEMETRY_PATH = Path(__file__).parent / "telemetry.jsonl"
MAX_SIZE = 10 * 1024 * 1024  # 10 MB
BACKUP_COUNT = 3             # Keep 3 rotated backups (~30MB total)


def log_event(event_type: str, data: dict) -> None:
    """Append a structured JSON line to telemetry.jsonl."""
    entry = {
        "ts": datetime.now(timezone.utc).isoformat(),
        "type": event_type,
        **data,
    }
    line = json.dumps(entry, separators=(",", ":")) + "\n"

    try:
        try:
            if TELEMETRY_PATH.stat().st_size > MAX_SIZE:
                _rotate()
        except FileNotFoundError:
            pass

        with open(TELEMETRY_PATH, "a") as f:
            f.write(line)
    except OSError as e:
        # Fallback to stderr (captured by journald)
        print(f"[telemetry] write failed: {e}", file=__import__("sys").stderr, flush=True)


def _rotate() -> None:
    """Rotate telemetry files: .jsonl → .jsonl.1 → .jsonl.2 → .jsonl.3"""
    for i in range(BACKUP_COUNT, 1, -1):
        src = TELEMETRY_PATH.with_suffix(f".jsonl.{i - 1}")
        dst = TELEMETRY_PATH.with_suffix(f".jsonl.{i}")
        if src.exists():
            dst.unlink(missing_ok=True)
            src.rename(dst)
    backup = TELEMETRY_PATH.with_suffix(".jsonl.1")
    backup.unlink(missing_ok=True)
    TELEMETRY_PATH.rename(backup)


# === Ops logging (goes to journald via stdout) ===

def log(msg: str) -> None:
    """Human-readable operational log line. Captured by journald."""
    ts = datetime.now(timezone.utc).strftime("%H:%M:%S")
    print(f"[{ts}] {msg}", flush=True)

Usage:

# Operational (human reads via journalctl -u myservice -f)
log("Refreshing token for account X")
log("Switch: account A → account B (reason: 5h breach)")

# Telemetry (machine reads via jq/DuckDB/Claude Code)
log_event("token_refresh", {"account": "X", "expires_in_h": 8.0, "token_fp": "abc12345"})
log_event("account_switch", {"from": "A", "to": "B", "reason": "5h_breach"})

Security: Token Fingerprinting (Not Regex Redaction)

Never pass secrets through the logging pipeline. Log only a non-reversible fragment:

def _token_fingerprint(token: str) -> str:
    """Extract uniquely identifiable chars from a token's mid-section.

    The prefix (sk-ant-oat01-) and suffix (...AA) are common across tokens.
    Chars 14-22 (after the prefix) are the most unique per-token.
    Middle-slice avoids leaking type-prefix metadata that prefix-based
    approaches expose.
    """
    if len(token) > 25:
        return token[14:22]
    return token[:8] if token else ""

# Usage: log the fingerprint, never the token
log_event("token_refresh", {"account": name, "token_fp": _token_fingerprint(token)})

Why this is superior to regex redaction filters:

This aligns with OWASP Logging Cheat Sheet: "Ensure that no sensitive data is included in log entries." Major platforms (AWS, Stripe, GitHub) use separate non-secret identifiers or partial token display — never full tokens with regex scrubbing.

Regex filters remain useful as a defense-in-depth backstop, not a primary control.

Health Endpoints as Observability

For small deployments, rich JSON health endpoints replace log aggregation:

@app.get("/api/status")
def status():