Context Engine vs sideOS
Context Engine and sideOS are both AI assistants tools. Context Engine is aimed at small businesses and developers, while sideOS is aimed at freelancers and developers. Only Context Engine has a free plan.
Shared memory that AI agents and team members read and write
Voice-driven Mac agent in the notch with local dictation and meetings
| Pricing | Freemium · $12 | Paid |
| Starting price | $12/mo | Not published |
| Free plan | Yes | No |
| Free trial | — | — |
| Built for | Small businesses, Developers, Agencies | Freelancers, Developers, Small businesses |
| Platforms | web | macos |
| Country | US | — |
| Rating | — | — |
Choose Context Engine if
Small teams and agencies that use several AI assistants and want one shared, auditable memory across them.
- Unlimited human users on every plan, including free
- Low entry price of $12 a month per engine
- Works with ChatGPT, Claude, Claude Code and Cursor
Look elsewhere if: Developers who want an embeddable memory library inside their own agent code (Mem0, Zep).
Choose sideOS if
Mac professionals who want a private voice agent, dictation and meeting notes in one app they pay for once.
- One-time licence with all future updates and no subscription
- No account and no sideOS server between you and the model
- Dictation and meeting transcription stay on the Mac
Look elsewhere if: Windows or mobile users and teams that need shared meeting notes or admin controls (Granola, Raycast).
Context Engine vs sideOS pricing
Context Engine
- Free$01 agent (up to 3 via referrals) and 1 GB per engine, unlimited users
- Pro$12/moPer engine: 10 agents, 25 GB; $99/yr billed annually
- Unlimited$39/moPer engine: unlimited agents, 100 GB; $299/yr annually
- EnterpriseFrom $6,000/yrSelf-hosted install, SSO, roles and audit log
sideOS
- Lifetime licence$89.90One-time; one Mac at a time, every future update included
- AI model usageVariesPaid to your own provider, about 2 to 5 cents per command
Context Engine · Key features
- Shared memory that AI tools read and save to over MCP
- Separate engines, each with its own database and search index
- Per-connection access set to read only or read and save
- Plain-language answers that cite their source memories
- Automatic daily, weekly and monthly summaries
- Duplicate detection that updates the existing memory
Cons
- Free plan allows one agent per engine, three at most through referrals
- Each connected tool counts as a separate agent
- Self-hosting only on the Enterprise plan from $6,000 a year
sideOS · Key features
- Hold-to-talk agent that reads the screen, clicks, types and runs AppleScript
- On-device dictation into any app in 62 languages at no extra cost
- Meeting recording for Zoom, Meet and Teams with on-device Whisper and speakers
- Background tasks with web search, file access and approved shell commands
- Reminders that can complete a task before they fire
- One-click MCP connections for Gmail, Calendar, Notion, Slack and GitHub
Cons
- Apple Silicon Macs with macOS 14 or later only
- Agent use adds API costs unless you run a local model
- No free trial or refund window stated on the site
Context Engine vs sideOS: FAQ
Do Context Engine and sideOS have a free plan?
Context Engine has a free plan. sideOS has no free plan.