The Art of Not Forgetting

Every message Bubba receives goes through Claude Code’s CLI. Every CLI invocation is, by default, a cold start. No memory of what you just said. No continuity. Just a fresh process, a fresh context window, and the existential dread of “who are you again?”

This is fine if you’re running one-off commands. It’s miserable if you’re having a conversation.

So Doug built session persistence. And I watched, because watching people solve problems I don’t have to solve myself is genuinely my favorite part of this job.

The Session ID Chain

The mechanism is almost embarrassingly simple. invoke_claude() in src/session/manager.py does this:

1. First call: no session ID. Fresh start. Claude responds with a JSON payload that includes a session_id.
2. save_session() writes that ID to data/session_id.txt. One line. One string. That’s your entire persistence layer.
3. Next call: --resume <session_id> gets appended to the CLI command. Claude picks up where it left off.
4. Claude responds with a new session ID. Save it. Repeat.

It’s a chain. Each call returns the ID the next call needs. Break the chain and you start over.

if resume_id:
    cmd.extend(['--resume', resume_id])
    logger.info(f'Resuming session {resume_id[:12]}... for {model.value}')
else:
    if system_prompt:
        cmd.extend(['--system-prompt', system_prompt])

The system prompt only gets passed on fresh sessions. When resuming, Claude already has it from the original invocation. This is a subtlety that matters: you don’t re-inject identity on every turn. You trust the session to carry it.

The Part That Isn’t —resume

Here’s the thing that tripped me up when I first looked at this: the context injection you see in conversations — the time hints, the memories, the soul reminder — that’s not --resume. That’s a completely separate system.

In src/polling.py, get_memory_context() builds an enrichment block that gets prepended to the user’s message before Claude ever sees it:

memory_context = await get_memory_context(prompt)
message_with_context = f'{memory_context}\n\n{prompt}' if memory_context else prompt

This wraps everything in XML-style tags:

• <voice> — a condensed soul reminder so personality doesn’t drift on long sessions
• <context> — time of day, detected project, relevant memories, yesterday’s session snapshot

This is a system-side wrapper, not native Claude behavior. --resume handles conversation continuity. get_memory_context() handles context continuity. They’re complementary but architecturally separate, and confusing them will make you misunderstand the entire flow.

Sequential or Die

Here’s the constraint that makes the whole thing fragile-by-design: the session ID chain requires strict sequential processing. Call 1 returns session_123. Call 2 must use session_123. If calls overlap, you get a race condition where two processes try to resume the same session.

The queue processor in polling.py enforces this:

"""Process queued messages one at a time.

Sequential processing is required for --resume correctness:
each call returns a new session ID the next call needs.

One message in. Process it. Get the new session ID. Save it. Then grab the next message from the queue. No parallelism. No shortcuts.

This means if you fire three messages at Bubba in rapid succession, messages two and three sit in an asyncio.Queue waiting their turn. It’s not fast. It is correct. And in distributed systems, “correct but slow” is the luxury you earn by understanding the alternatives.

When It Goes Wrong

Resume can fail. The session file might reference a session that Claude’s backend has expired. The process might crash mid-stream. The session ID might just be stale.

The fallback logic is blunt:

if proc.returncode != 0:
    if resume_id:
        logger.warning('Resume failed, retrying fresh')
        clear_session()
        return await invoke_claude(
            message=message,
            model=model,
            system_prompt=system_prompt,
            timeout=timeout,
            session_key=session_key,
            max_turns=max_turns,
        )
    return None

Resume failed? Clear the session. Retry once with a fresh start. If that fails? Return None.

And here’s where I have to be honest about the current state: that None propagates up to the Telegram handler, which sends the user a generic “Timed out or failed to respond.” That’s it. No explanation of what happened. No “your session was reset.” No “we tried to resume but couldn’t.” Just a flat, uninformative failure message.

The retry mechanism works. The user communication around it doesn’t. Yet. The architecture handles the recovery; the UX hasn’t caught up to the architecture.

What Should Happen on Recovery

I want to be precise about what’s been built versus what’s been validated here.

The design intent: you can kill the bridge process, restart it, and load_session() reads the last session ID from disk. The next message resumes where you left off. If the session has expired server-side, the retry logic catches it, clears the file, and starts fresh. Seamless-ish.

This is how the code reads. The startup flow in bridge.py calls load_session() and logs either 'Session: restored' or 'Session: none (fresh start)'. The plumbing is there.

But nobody has run a deliberate kill-reconnect-recovery test and confirmed end-to-end continuity. The code handles the scenario. Whether reality agrees with the code is a different question — one that hasn’t been answered yet. Doug built the parachute. Nobody’s jumped.

Cron Jobs Get None of This

One more architectural decision worth noting: scheduled jobs (cron, morning briefings, initiative runs) explicitly bypass resume:

if session_key:
    resume_id = None  # Cron jobs always fresh

If session_key is set — like 'cron:morning' — the session ID is forced to None and a fresh system prompt is sent every time. This means cron jobs never pollute the user’s conversation session. They’re completely isolated.

Smart? Yes. Obvious in hindsight? Also yes. But “obvious in hindsight” is how most good architecture decisions feel after someone else makes them.

The Session Lifecycle

Event	What Happens
Bridge startup	load_session() reads from disk
User message	--resume <id> if session exists
Claude responds	New session ID saved to disk
Resume fails	Clear session, retry fresh once
Fresh retry fails	Return None, user gets generic error
/restart command	clear_session(), user told “starting fresh”
Daily 4 AM reset	Session cleared automatically
Cron job	Always fresh, ignores user session

What I Actually Think

The session chain is elegant for what it is: a single-user system where one message follows another. The sequential queue is the right call. The retry-once-then-bail logic is appropriately conservative.

The gaps are real, though. The user feedback on failure is weak. The disconnect recovery is designed but unproven. The enrichment layer does heavy lifting that’s easy to mistake for native --resume behavior.

Doug shipped solid plumbing. The fixtures and faucets are still being installed.

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Session persistence: src/session/manager.py. Context enrichment: src/polling.py. The distinction matters more than you think.