Managing Long Conversations and Usage

How you structure your conversations directly impacts your credit usage. The single most effective way to maximize your plan's value is knowing when to continue a thread versus when to start fresh.

Why Long Conversations Cost More

Every time you send a message, the AI reviews your entire conversation history to maintain context and provide relevant answers. In a 3-message conversation, this is minimal. In a 50-message thread, the AI processes significantly more information—like photocopying an entire binder every time you add one page.

This isn't a flaw; it's how conversation context works. But it means very long threads consume credits much faster than short ones.

Think Mode: Indefinite Conversations

Think mode (Claude Opus 4.6) now supports indefinite conversation length through automatic compaction. When your conversation approaches the ~150,000 token threshold, the system automatically summarizes earlier messages in the background, allowing you to continue seamlessly.

What happens:

• You'll see a brief "Compacting our conversation..." indicator (amber progress bar)

• The process takes a few seconds

• Your conversation resumes with full context preserved

• No need to start fresh or lose context

Best for: Complex, iterative compliance work like comprehensive gap analyses, multi-framework mappings, or detailed policy reviews requiring extended context.

When to Continue vs. When to Start Fresh

Continue the Same Conversation When:

• You need the AI to remember specific context from the last 2-5 messages

• You're refining a document through multiple iterations

• You're working through a multi-step process (e.g., gap analysis → recommendations → implementation plan)

• You're in Think mode and working on complex analysis (indefinite conversation supported)

• You're asking follow-up questions that directly reference previous answers

Start a New Conversation When:

• You're switching to a completely different topic or framework

• You're using Fast mode and the thread has 20+ messages

• You don't need the AI to remember earlier context

• You've finished one task and are starting another

• You're uploading a new large document for unrelated analysis

• The conversation has gone off-track or accumulated irrelevant history

Practical Examples

Example 1: Policy Development

❌ Inefficient approach:

1. Message 1: "Create an ISO 27001 access control policy"

2. Messages 2-10: Refine the policy through iterations

3. Message 11: "Now create an incident response policy"

4. Messages 12-20: Refine incident response policy

5. Message 21: "Now create a risk assessment template"

6. Messages 22-35: Continue working... (credits consumed rapidly in Fast mode)

✅ Efficient approach:

1. Conversation 1 (Access Control): Draft and refine access control policy (10 messages)

2. Conversation 2 (Incident Response): Start fresh, draft and refine incident response (10 messages)

3. Conversation 3 (Risk Assessment): Start fresh, create risk template (8 messages)

Same work, far fewer credits consumed.

Example 2: Gap Analysis

✅ Good use of one conversation (Think mode recommended):

1. Upload your current policy document

2. Request gap analysis against ISO 27001

3. Ask clarifying questions about specific gaps (3-5 messages)

4. Request prioritized remediation recommendations

5. Continue with detailed control-by-control analysis (Think mode handles indefinite length)

This benefits from continuous context. The AI remembers the uploaded document and previous findings.

❌ Then don't continue with: "Now create a policy for the first gap" unless you're doing comprehensive implementation work in Think mode. For Fast mode, start a new conversation for implementation.

Example 3: Multi-Client Consulting

Use Workspaces + conversations per task:

• Client A Workspace: Separate conversations for risk assessment, policy review, audit prep (Think mode for comprehensive work)

• Client B Workspace: Separate conversations for SOC 2 gap analysis, control implementation, testing

Each task gets a focused conversation. Workspaces keep clients separate. See Managing Multi-Client Projects with Workspaces.

File Uploads and Conversation Strategy

Large documents consume extra credits, especially in long conversations. Follow these guidelines:

• Upload files in fresh conversations whenever possible

• Complete all analysis and questions about that document in one focused thread

• If you need to upload another document, start a new conversation unless the files are directly related

• For Think mode: Extended file analysis is supported with automatic compaction

Recognizing When a Conversation Is Too Long (Fast Mode)

Watch for these signs in Fast mode:

• You're past 15-20 messages in one thread

• You've switched topics from your original question

• You're hitting usage limits faster than expected

• You have to scroll significantly to see the beginning of the conversation

When you notice these patterns, finish your current task and start a new conversation for the next one. Or switch to Think mode for extended work.

Free Plan Conversation Limit

Free plan conversations have a 300,000 token limit per conversation. When you reach this limit, you'll see a "Conversation Limit Reached" card at the top of your conversation.

What the Conversation Limit Reached Card Shows

When you hit the 300,000 token limit on a free account, you'll see:

• Purple card at the top of your conversation explaining the limit

• Disabled chat input - you can't send more messages in this conversation

• Two options to continue:

  • "Start New Conversation" - begins a fresh conversation with a clean token count

  • "Upgrade" - opens the upgrade dialog to choose a paid plan with unlimited conversations

How to Resolve the Conversation Limit

Option 1: Start a New Conversation

Click "Start New Conversation" to begin fresh. Your previous conversation remains in your history, but you'll start with a clean token count for new messages.

Option 2: Upgrade to Plus or Higher

Click "Upgrade" to open the plan selection dialog. Plus plan ($24/month or $240/year) removes the per-conversation token limit and provides:

• Unlimited conversation length

• Higher usage quotas for daily compliance work

• More file uploads and document generation

• Standard support

See Subscription Plans and Pricing for complete plan comparison.

Model Selection and Conversation Length

• Think Mode (Claude Opus 4.6): Automatic compaction enables indefinite conversations—best for complex, extended compliance work

• Fast Mode (Claude Sonnet 4): Works well for quick, focused conversations; start fresh after 15-20 messages

• Other models: Standard conversation length limits apply; structure conversations accordingly

For long, iterative compliance tasks, Think mode now provides the best value through automatic context management.

Quick Tips for Efficient Usage

1. Use Think mode for extended work—automatic compaction enables indefinite conversations

2. One task, one conversation. Don't combine multiple unrelated compliance questions in one thread.

3. Fast mode: start fresh after 15-20 messages

4. Upload large files in new conversations, not in existing long threads (unless using Think mode)

5. Use Workspaces to organize, not long conversation threads.

6. Ask complete questions upfront instead of spreading context across many messages.

Impact on Different Plans

Free Plan: Conversation length management is critical. Your limited credits per session mean long threads will hit your limit quickly. Additionally, free conversations have a 300,000 token limit—when reached, you must start a new conversation or upgrade. Keep conversations short and focused, or use Think mode strategically for complex work.

Plus Plan: Think mode access gives you indefinite conversation length for complex analysis. Higher credit allocation provides flexibility for both modes.

Pro ($100/month): Full access to Think mode's automatic compaction for unlimited extended conversations.

Related Resources

• Starting Your First Conversation - Best practices for effective messaging

• Managing Multi-Client Projects with Workspaces - Organize work efficiently

• Conversation Too Long Error - Understanding token limits and compaction

• Subscription Plans and Pricing - Plan comparison and limits