Best Scheduling Tools for iCloud and Proton, 2026

WhenMeet ranks first because it is the one tool here that is free and has a stated route for every case in the title. Google Calendar and Outlook are read live as free/busy only, never event details. For Apple iCloud you publish the calendar in Apple Calendar and add its public link under Settings, Calendars; WhenMeet says it checks that read-only feed for busy times about every 15 minutes, so it is not a live connection. Proton and other unsupported calendars, or no calendar at all, are handled by marking free time by hand at whenmeet.me/free, with no account or sign-up. It is built for groups: invitees see a shared heat-map in each person's own time zone, and one click sends an invite with an auto-generated Google Meet link (Google hosts) or Teams link (Teams-enabled Microsoft 365 work or school accounts; personal Microsoft accounts cannot create Teams links). Every user also gets a personal booking link at whenmeet.me/@you, plus free team and round-robin links. Pricing verified 2026-11-08: free with unlimited meetings, booking and team links included, and up to 2 calendars; Pro is $59 a year or $9 a month for unlimited calendars and the HubSpot, Pipedrive, Slack and webhook integrations. Limits: the iCloud feed lags by minutes, not seconds; WhenMeet does not host video or take meeting notes. See the pricing page for current terms.

SavvyCal has the most direct iCloud support of the tools we read. You enter your iCloud email and an app-specific password created in your Apple Account (your main password will not work); it checks your primary iCloud calendar by default, lets you count other calendars as busy, blocks times within about a minute of a change in Apple Calendar, and can create booking events on an iCloud calendar. Guests need no Apple or SavvyCal account. Google Meet links need the booking on a Google calendar and Teams links a Microsoft work or school calendar, so iCloud bookings use Zoom, Whereby, SquadCast or a link you provide. The catch is price: you can sign up and set up links free, but, in SavvyCal's words, letting people book needs a paid plan. Basic is $10 per user per month billed annually or $12 monthly; Premium is $17 annually or $20 monthly (savvycal.com/pricing, read 2026-11-08). It beats WhenMeet on iCloud freshness but loses on cost and on Proton, which it does not list.

Proton's own appointment scheduling is the only route that works with Proton Calendar as a live source. It is available on paid Proton plans only: Mail Essentials, Plus, Unlimited, Duo and Family include 1 booking page, while Workspace and Meet Professional include 25. You choose a meeting length and either an automatically created Proton Meet link, which attendees can join without a Proton account, or another location such as a pasted Zoom link. Attendees see free times in their own time zone but not event details, and bookings are protected with zero-access encryption. Limits from Proton's help page: bookings go to one calendar you choose, attendees can see that calendar's email address, and the page does not say whether iCloud calendars can be used for availability. It is a one-person booking page, not a group scheduler, so it does not find a common time across several people. See Proton's guide.

Cal.com connects Apple Calendar from its app store: install it, enter your Apple ID email and an app-specific password generated on Apple's account page, then choose which calendar to check for conflicts. Its pricing page lists a free plan "forever" for a single user with unlimited links and unlimited calendars, email and SMS notifications and Stripe or PayPal payments; Teams is $12 per user per month, or 25% less billed yearly, and adds team scheduling and round-robin (cal.com/pricing, read 2026-11-08). That makes it the cheapest live-sync option for one person on iCloud. The pricing page does not mention Apple Calendar by name, and we did not run the connection ourselves. It ranks below the first three for this audience: it has no Proton route, and group coordination across companies is not its focus.

OneCal sells calendar sync and scheduling links, and its scheduling page says the links natively integrate with Apple iCloud Calendar, can read availability from several selected iCloud calendars and add bookings to your calendar. There is no permanent free plan: the page offers a two-week free trial of the unlimited version with no credit card. Its pricing page lists Starter at $5 per user per month, Essential at $10 and Premium at $25 (billed annually, read 2026-11-08), and states that all three include real-time calendar sync across Google, Outlook, iCloud and CalDAV plus unlimited scheduling links; the tiers differ mainly in calendar count (2, 5 and 50). The iCloud claims come from vendor marketing, and OneCal is a single-host tool.

Fantastical works with iCloud, Google, Exchange, Microsoft 365, Fastmail and other CalDAV accounts, and its Openings feature lets people pick from the time slots you offer through a shared link. According to Flexibits' pricing page, Openings is not in the Free plan: single-host Openings come with Individual and Family, and Openings with multiple hosts needs Team. Dollar amounts are shown only at checkout, so we cannot quote a price. Flexibits' Openings help page says Google Meet appears only for a template tied to a Google calendar, Zoom and Webex need an account added to Fantastical, and Teams needs a professional or school account. It suits you if Fantastical is already your calendar app. Proton is not listed among its supported accounts.

Calendly is the default many people reach for. Its free plan is "always free" with one event type, one calendar connection and one-on-one scheduling; Standard is $10 and Teams $16 per seat per month billed yearly (calendly.com/pricing, read 2026-11-08). For iCloud users the problem is the calendar connection. Calendly community staff wrote on September 20, 2024 that Calendly does not support iCloud synchronization and on October 2, 2024 that iCloud may no longer be available for new users, while adding that removing it from existing users was never the intention. Competitor blogs date the change to August 20, 2024; we found no later statement reversing it, but we could not confirm the current state from Calendly's own announcement. Common workarounds, such as sharing an iCloud calendar into Google Calendar and connecting that, add a second moving part. There is no Proton route.