Feature request: Recognize cross-session context signals when memory is enabled

Preflight Checklist

• [x] I have searched existing requests and this feature hasn't been requested yet
• [x] This is a single feature request (not multiple features)

Problem Statement

Problem

When memory is enabled, Claude Code still treats each session as isolated by default. It doesn't recognize linguistic or contextual signals indicating the user expects continuity from prior sessions.

Linguistic signals that imply cross-session context

• Pronouns: "we", "our", "us"
• References to prior work: "the thing we built", "where we left off", "the fix we made"
• Assumptions of shared knowledge: "you know the one", "like before", "as we discussed"

Current behavior

Claude interprets these references against only the current session state, leading to confusion when that state doesn't match the user's expectations. The user must explicitly re-establish context that memory should already provide.

Expected behavior

When memory is enabled and the user's language implies shared history, Claude should:

1. Recognize these signals as potential references to prior session context
2. Proactively query memory or search for relevant artifacts (files, branches, prior work)
3. Clarify if ambiguous rather than assuming current session state is the reference

Core insight

Memory storage alone isn't sufficient—Claude needs intent detection to know when to leverage stored memory based on conversational cues.

Proposed Solution

When memory is enabled and Claude detects linguistic signals implying cross-session context ("we", "our", "where we left off", etc.), Claude should:

1. Check memory first - Before assuming current session state is the reference, query stored memory for relevant prior context (recent branches, files worked on, project state)

1. Surface ambiguity - If current session state doesn't match likely prior context, ask a clarifying question like: "Are you referring to [X from memory] or [Y from current session]?"

1. Proactive search - When references are ambiguous, use available tools to search for context (e.g., git branch -r | grep <username>, recent file modifications, etc.)

Example interaction

User: "Let's continue where we left off on our branch"

Current behavior: Claude assumes the currently checked-out branch is "our branch"

Proposed behavior: Claude recognizes "we" and "our" as cross-session signals, checks memory for recently worked branches, and either:

• Switches to the remembered branch automatically, or
• Asks: "I see you're on claude/new-session-xyz. Did you mean josha/tceg-smart-resize from our previous session?"

Alternative Solutions

_No response_

Priority

Critical - Blocking my work

Feature Category

CLI commands and flags

Use Case Example

_No response_

Additional Context

_No response_