Conversational Context Loss

The Problem

Agent loses track of multi-turn conversation, failing to maintain coherent dialogue or reference previous exchanges appropriately.

Symptoms

• ❌ Asks same question twice

• ❌ Ignores user's clarifications

• ❌ Restarts topic already discussed

• ❌ Pronouns become ambiguous ("it", "that")

• ❌ Cannot follow conversation thread

Real-World Example

Turn 1:
User: "How do I reset my password?"
Agent: "Click 'Forgot Password' on the login page."

Turn 2:
User: "I don't see that button"
Agent: "To reset your password, click 'Forgot Password'."
→ Repeated same answer, ignored "I don't see button"

Turn 3:
User: "What about it?"
Agent: "What are you asking about?"
→ Lost context: "it" = "Forgot Password button"

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Deep Technical Analysis

Context Dependency

Anaphora Resolution:

User: "Show me authentication docs"
Agent: [Provides docs]
User: "Can you explain it?"

"it" refers to: "authentication"
Agent must resolve pronoun to original topic

Without context:
→ Agent: "What would you like explained?"
→ Lost reference

Implicit References:

Turn 1: User asks about "Project Phoenix"
Turn 2: User says "Update me on its status"

"its" = "Project Phoenix's"
Agent needs conversation history to understand

Follow-Up Handling

Clarifications:

User: "Rate limit?"
Agent: "API rate limit is 1000/hour"
User: "For which plan?"

Agent must recognize:
→ Follow-up question
→ Refines previous query
→ Answer: "1000/hour applies to Premium plan"

Not: Treat as new independent question

Corrections:

User: "What's the rate limit?"
Agent: "100 per hour"
User: "No, I mean the new rate limit"

Agent should:
→ Recognize correction
→ Search for "new rate limit"
→ Provide updated info

Not: Stick to "100/hour"

Conversation Threading

Topic Tracking:

Maintain topic stack:
→ Turn 1: Topic = Authentication
→ Turn 2: Topic = OAuth (subtopic of Authentication)
→ Turn 3: "What about rate limits?" → New topic

Topic stack: [Authentication > OAuth] → [Rate Limits]

Enables:
→ "Go back to authentication" (pop stack)
→ Context-aware responses

Intent Chaining:

Turn 1: Intent = "explain_concept" (authentication)
Turn 2: Intent = "clarify" (specific OAuth step)
Turn 3: Intent = "troubleshoot" (OAuth not working)

Intent sequence matters:
→ From explain → clarify → troubleshoot
→ Progressive problem-solving

Not: Independent queries

Context Window Management

Sliding Window:

Include last N turns:
→ N=5: Last 5 exchanges always in context

Turn 20:
→ Includes turns 16-20
→ Drops turns 1-15

Problem:
→ User references turn 3 in turn 20
→ Turn 3 not in context
→ Agent can't answer

Relevant Turn Retrieval:

Instead of sliding window:
→ Always include recent 3 turns
→ Retrieve relevant older turns

Turn 20: "What was my project again?"
→ Retrieve turn 1: "I'm on Project Phoenix"
→ Agent: "Your project is Phoenix"

Semantic memory

Conversation State

User Intent Tracking:

Track user's goal across turns:
→ Goal: Set up authentication
→ Progress: 
  - Step 1: Understood OAuth ✓
  - Step 2: Got credentials ✓
  - Step 3: Implementing... (current)

Agent aware of:
→ Where user is in process
→ What's already covered
→ What's next

Disambiguation Prompts:

User: "Tell me about it"

Agent detects ambiguity:
→ Multiple "its" possible in context
→ Prompt: "Are you asking about:
  A) The authentication flow we discussed?
  B) The rate limiting policy?"

User clarifies: A
→ Context maintained

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How to Solve

Include last 3-5 turns in context always + use semantic retrieval for relevant older turns + implement pronoun/anaphora resolution (replace "it" with actual referent) + track conversation topics and intents + detect follow-ups and clarifications (not new queries) + maintain conversation state (user's goal, progress) + prompt for disambiguation when reference unclear + test multi-turn conversation scenarios + measure conversation coherence score. See Conversation Context.