Reclaim.ai is an AI scheduling assistant. It plans your tasks, defends your focus time, and copies events between calendars.
Keeper.sh is the Reclaim.ai alternative when you want flat $5 a month busy-block sync, or free to start, that reaches iCloud, Fastmail and CalDAV — not AI scheduling limited to Google and Outlook.
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).
On Pro, Google and Microsoft notify Keeper.sh the moment an event changes, so the copy is written within seconds. iCloud, Fastmail and other CalDAV calendars are read on a timer instead, because Apple publishes no way for a calendar tool to be told an event changed. On Free, linked calendars update about every 30 minutes.
Reclaim's instant claim applies to Google and Outlook Calendar Sync. That speed is a product fact, not a reason to leave the busy-block job when your calendar lives on iCloud or CalDAV.
Keeper.sh reaches further out in time. It covers a month back and two years ahead by default, so a specialist appointment booked eighteen months early is blocked from the day you make it. Pro can change that span.
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 both calendars should stay in step (syncing in multiple directions). Keeper.sh wants two mappings, one pointing each way (A to B and B to A).
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 annually, Starter, Business and Enterprise are $10, $15 and $22 per seat per month. Billed monthly, Starter is $12 and Business is $18; Enterprise is not offered monthly. 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 free for 2 linked accounts and 3 connections, with no limit on how many calendars each account exposes. Pro is $5 a month, or $45 a year, and lifts both limits. On Pro, Google and Outlook copies land within seconds, and you can 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 Reclaim.ai has that Keeper.sh does not
These are product differences, not reasons to leave the busy-block job for Reclaim.
AI week planning. Reclaim ships AI Agents for Focus Time, Habits, Buffer Time, Smart Meetings and Meeting Quality, plus task planning on Google and Outlook calendars. Keeper.sh does not plan your week.
Scheduling links. Reclaim includes booking and scheduling links on its plans. Keeper.sh ships none today.
Team seats with SSO. Enterprise adds SSO and SCIM user provisioning. Keeper.sh is set up one person at a time.
Instant Google and Outlook sync. Reclaim markets Calendar Sync updates as immediate on the two calendar services it supports. Keeper.sh matches that notify path on Pro for Google and Outlook; iCloud and CalDAV stay on a timer for every tool.
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?
Keeper.sh, when any calendar you care about lives on iCloud, Fastmail or CalDAV, or you want free-to-start flat $5 busy-block sync and one link that shows your availability everywhere. That is the job this page is for.
Reclaim's AI Agents, Lite free sync on Google or Outlook, scheduling links, and Enterprise SSO stay in the facts section above — they are not a second winner on this page.
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 signed-in iCloud with an app-specific password you generate in your Apple account. That same Apple ID can be source and destination via two mappings; a pasted share link or subscribed feed is pull-only and cannot be a destination.
Does Keeper.sh keep both calendars showing the same busy time?
Yes. Each connection copies busy blocks one way, so you add one mapping each way (A to B and B to A) when both calendars should stay in step. Guest lists are never copied.
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.
Other comparisons
Still weighing tools? These cover the rest of the field.
- Keeper.sh vs CalendarBridge
- Keeper.sh vs Kalender Sync
- Keeper.sh vs Morgen
- Keeper.sh vs OneCal
- Keeper.sh vs SyncDate
- Keeper.sh vs SyncThemCalendars
- Nine calendar sync tools compared on price, speed and privacy
Sources
Every claim about Reclaim.ai above comes from Reclaim's own public pages, linked inline. Those pages were checked on 10 September 2026, and Reclaim may have changed since.