Microsoft Outlook Calendar vs Tilly

Microsoft Outlook Calendar provides calendar and email access through web, desktop, and mobile apps, including iOS and Android. Outlook Free includes email and calendar, 15 GB of mailbox storage, 5 GB of cloud storage, and core security features such as spam filters. Shared calendars and video meeting support are listed. Outlook can connect Outlook.com, Gmail, Yahoo!, iCloud, and other mail services, and scans links and attachments for threats. Focused inbox, sweep, snooze, and flags help organize email, while access to Word, Excel, PowerPoint, and OneDrive files is also included. Copilot can draft messages and help adjust tone, length, and clarity, but in Outlook it currently works with outlook.com, hotmail.com, live.com, and msn.com addresses. Microsoft 365 Personal costs $9.99 a month, billed monthly, and includes 1 TB of storage and use on five devices. Personal, Family, and Premium offer a one-month free trial, and paid Microsoft 365 plans include ongoing support. Subscriptions renew automatically unless canceled in the Microsoft account.

Tilly combines calendars and tasks in a daily plan, with a brief that highlights what is coming up, conflicts, and open time. It connects Google Calendar, Outlook and Microsoft 365, iCloud, CalDAV servers, and subscribed ICS feeds. Tasks appear alongside calendar events so users can judge them against available time. Booking links use availability across connected calendars while showing guests open times, not the events behind them. Tilly checks for overlaps across visible calendars; Pro can recommend which meeting to move and which to keep. It reads calendars into one view without copying events or busy blocks between accounts. Assistant-prepared calendar or task changes wait for explicit approval. Tilly is available on iOS, macOS, and the web. The Free plan supports two calendar accounts and costs nothing. Tilly Pro costs $7.99 a month, and Tilly Pro Annual costs $59.99 a year; eligible new subscribers can get a 14-day trial. Tilly says calendar data is encrypted in transit and at rest and is not sold to third parties.