Keeper.sh vs Reclaim.ai

Reclaim.ai is an AI scheduling assistant. It plans your tasks, defends your focus time, and copies events between calendars.

Keeper.sh does the copying, and reaches calendars Reclaim cannot: iCloud, Fastmail and any CalDAV server. That difference decides most of this comparison.

Which calendars can each one connect?

This is the sharpest split between the two products.

Reclaim's Calendar Sync covers Google and Outlook. Their help centre says it "is only supported for calendars connected to a Google Calendar or Microsoft Outlook account" (Calendar Sync overview). The same article suggests sharing an iCloud calendar into Google as a workaround, and notes this may cause delays.

Keeper.sh connects to Google, Outlook, iCloud, Fastmail, and any CalDAV server. It also reads public calendar links, though it cannot write events back to those.

So if your personal calendar lives on iCloud, or on a Nextcloud or Radicale server you run yourself, Keeper.sh reaches it with no shared-calendar workaround in the middle. That is the most common reason people end up here.

How fast do copies appear?

Reclaim says its copies are immediate, and their product page states: "Updates happen instantly—not on a timer or slow refresh" (AI Calendar Sync).

Keeper.sh reads your calendars every minute, on every plan. On Pro a new meeting lands on your other calendar in about a minute, two at the outside. On the free plan it is usually about fifteen minutes, and thirty-one at the very most.

If you need a personal event blocked at work within seconds, Reclaim is quicker on the two calendar services it supports.

Keeper.sh reaches further out in time. It covers a month back and two years ahead, so a specialist appointment booked eighteen months early is blocked from the day you make it.

Do both tools create duplicate events?

Yes, both of them do. A copy is the only thing another person's calendar can see.

Reclaim's help centre puts it plainly. Calendar Sync "has to create copies by design" (handling duplicates). Without the copy, a colleague looking at your work calendar sees that time as free, and Keeper.sh works the same way.

Both tools also copy in one direction at a time. Reclaim tells you to "set up two sync policies" when you want both ways (syncing in multiple directions). Keeper.sh wants two connections, one pointing each way.

What does a copied event look like?

Reclaim gives you a set of visibility choices on each policy. You can pick a Personal, Work, or Travel Commitment, "Busy for all", or two levels of detail sharing (sync policies).

You can also keep single events out by adding #nosync to the description (using #nosync). Their policy settings include a "Sync outside of working hours?" toggle and three separate rules for all-day events.

Keeper.sh anonymises copies by default, on both plans. A calendar you connect is copied out under the name of the calendar it came from, with the description and location stripped.

So a dentist appointment on a calendar you called "Personal" shows up at work as "Personal". Right day, right time, no detail.

Reclaim lets any plan, Lite included, choose how much detail travels. On Keeper.sh the private version is what you get by default, and changing it is a Pro feature.

Reclaim's filters also work per event, with working-hours rules and a keyword you type into an event. Keeper.sh filters per calendar instead: all-day events, focus time and out-of-office blocks, on Pro.

What does each one cost?

Reclaim's Lite plan is free and includes one Calendar Sync between two connected Google or Outlook calendars (pricing). Paid tiers are $10, $15, and $22 per seat per month for Starter, Business, and Enterprise. Enterprise is where SSO and SCIM user provisioning live.

None of those tiers add a calendar service, so paying more does not get you iCloud or CalDAV.

Keeper.sh is $0 or $5 a month, flat, for one person. Our free plan gives you two linked accounts and three connections, with no limit on how many calendars each account exposes.

Pro removes both limits. It also writes copies every minute, and lets you change what shows through on a copy.

Keeper.sh is priced per person rather than per seat, and there is no SSO or SCIM today.

What else does Keeper.sh give you?

It publishes one calendar link covering every calendar you pick. Hand that link to anyone who needs your availability, and event names show as "Busy" by default.

It has a REST API and an MCP server, both usable on the free plan at 25 calls a day. It costs $5 a month for a person, rather than a price per seat.

And it is open source under AGPL-3.0, so you can read every line of code that touches your calendar.

Can you run Keeper.sh yourself?

Yes, and you get the full product. The whole codebase is on GitHub under AGPL-3.0, with Docker images to make a first deployment quick.

Self-hosting turns on every Pro feature at no cost, deliberately. Running our code on your own hardware gets you the same product we host.

It is genuine work, though. You need somewhere to run it, a Postgres database, and Redis. You also register your own Google and Microsoft credentials, which takes an afternoon the first time.

After that, upgrades, backups, and uptime are yours to own.

Most people should use hosted Keeper.sh and pay the $5. Run it yourself if you want your calendar data on hardware you control.

So which should you pick?

Pick Keeper.sh if any calendar you care about lives on iCloud or Fastmail, or on a server Reclaim cannot reach. Pick Keeper.sh if you want more than three connections for a flat $5, or one link that shows your availability everywhere.

Reclaim's case is two Google or Outlook calendars on one free sync, AI task planning, and seats with SSO.

FAQ

Can Reclaim sync my iCloud calendar?

Not directly, on any plan. Their documentation limits Calendar Sync to calendars connected to a Google or Microsoft Outlook account, and suggests sharing iCloud into Google as a workaround. Keeper.sh connects to iCloud directly, using an app-specific password you generate in your Apple account.

Does Keeper.sh copy attendees or video call links?

No. A copy carries the times, the busy or free status, and whatever detail your settings let through.

Attendees, meeting links, and reminders are never copied across. Keeper.sh does read attendees, so you can see pending invites and RSVP.

Can I use both tools together?

Yes, though most people will not need to. Reclaim can handle scheduling on your Google and Outlook calendars while Keeper.sh covers an iCloud or CalDAV calendar it cannot reach.

Other comparisons

Still weighing tools? These cover the rest of the field.

Sources

Every claim about Reclaim.ai above comes from Reclaim's own public pages, linked inline. Those pages were checked on 11 August 2026, and Reclaim may have changed since.