AI Memory: The AI That Learns How You Work
AI Memory is an optional feature that allows SimpleAI to learn from individual users’ chat behavior over time. After approximately four messages in a conversation, the AI evaluates whether anything from the exchange is worth remembering and if it determines the insight is relevant, it creates a memory automatically.

Memories are personal to each user and are not shared across the organization. They feed into the AI’s outputs in both chat and playbook reviews, making responses progressively more aligned with how each person works.
How AI Memory works
Memory fills gaps in your User Context. If you’ve already told SimpleAI you prefer a moderate review posture, it won’t overwrite that; it will build on it. If there’s a nuance you haven’t articulated explicitly but demonstrate consistently in your work, Memory captures it.
What Memory does and doesn’t override
Memory sits at the bottom of the priority order:
- Playbook or session-specific instructions: always take precedence.
- Company Context: your organization’s standards. Memory never overrides these.
- User Context: your stated preferences. Memory fills gaps here; it doesn’t replace them.
- AI Memory: learned behavior that enhances everything above it.
This means organizational governance is always protected. Memory makes the AI smarter and more personalized, but it never makes it go off-policy.
In practice
Memory is most useful for preferences you haven’t explicitly written into User Context. If you always push back on a certain clause construction, or always ask for a specific fallback position, Memory learns that from your behavior rather than requiring you to articulate it upfront.
What Memory is not
Memory is personal. Each user has their own memory store and it’s never shared across the organization. It never influences how the AI behaves for other team members.
Memory is also not a substitute for AI Context. A well-configured Company Context and User Context are deliberate and explicit; they apply from the first interaction. Memory accumulates over time and fills in what context doesn’t cover.
Think of it this way: Context is the briefing you give the AI up front. Memory is what it picks up by working alongside you.
Staying in control
You have full visibility into what SimpleAI has remembered about you. Open your settings at any time to view your stored memories. If something isn’t accurate or no longer applies, delete it and changes take effect immediately.

Memory is also optional. If you’d prefer to turn it off entirely, you can do that in your settings. The AI will continue to benefit from whatever you’ve set in User Context; it just won’t learn from session behavior.

Note
Once Memory is enabled, check your stored memories after a few weeks of regular use to see what the AI has learned. Most users find the memories accurate, but a quick review early on ensures nothing has been picked up from an unusual session.
What changes over time
The AI stops asking for things you always provide. If you consistently ask for issues flagged by severity, Memory learns that and does it without being asked.
Outputs get more aligned with your style. Redline language, comment tone, and level of detail gradually reflect how you actually work; not how a generic user works.
Onboarding gets easier for consistent users. The more you use SimpleAI, the less you need to prompt it. Memory reduces the gap between what you expect and what you get.
Getting started
To enable Memory, turn it on in your personal SimpleDocs settings. The most useful thing you can do before enabling it is make sure your User Context is set up first (see the previous chapter), so Memory has a strong foundation to build on rather than doing all the work itself.
Once enabled, go to your settings after a few weeks of regular use and review your stored memories. Delete anything that doesn’t reflect your current preferences, and let the rest keep working.