Allow Scheduling Over Calendar Holds

By default, SkipUp respects all busy time on your calendar when finding meeting slots. If you use calendar holds — like focus time, to-do blocks, or personal reminders — you can allow the assistant to use those as a fallback when your availability is tight.

What this setting does

When enabled, SkipUp treats flexible calendar holds — like focus time and to-do items — as backup availability. The assistant first looks for times when you’re completely free. If there aren’t enough open slots, it will also consider times that overlap with flexible holds.

SkipUp reads the title of each block to distinguish flexible holds from real commitments. Committed blocks — like medical appointments or travel — are never used as fallback, even when availability is tight.

How SkipUp finds times

When looking for meeting slots, SkipUp follows this priority order:

1. Open time — Slots where you have no calendar events at all
2. Reduced buffer — Slots with less padding between meetings, if needed
3. Flexible holds — Slots that overlap with focus time or other flexible blocks (only when this setting is enabled)

The assistant always prefers genuinely free time. Your flexible blocks are only considered when open slots are limited.

What counts as flexible vs. committed

Block type	Used as fallback?
Focus time	Yes — when open times are limited
To-do / task blocks	Yes — when open times are limited
Placeholder holds	Yes — when open times are limited
Blocks from third-party tools (Reclaim, Clockwise)	Yes — when open times are limited
Medical / dental appointments	No — recognized as a commitment
Childcare / school pickup	No — recognized as a commitment
Travel / flights	No — recognized as a commitment
Out-of-office	No — always respected
Meetings with other people	No — always respected
All-day events	No — always respected

How to enable it

1. Go to your workspace and click Settings in the sidebar
2. Select Profile under Personal
3. Scroll to the Scheduling section
4. Toggle on Allow scheduling over calendar holds
5. Click Update Profile

The change takes effect immediately for all future scheduling.

Things to know

• Per-user setting — This applies only to your calendar. Other workspace members’ settings are independent.
• All connected calendars — The setting applies across all your connected calendars (Google and Microsoft).
• Title matters — SkipUp uses the title of your calendar blocks to decide whether they’re flexible. A block titled “Focus time” will be treated as available, while “Dentist at 3pm” will be respected. If you want a block to be treated as a commitment, give it a descriptive title.
• Fallback only — SkipUp always tries to find times when you’re completely free first. Your flexible blocks are only used when there aren’t enough open slots available.
• Out-of-office is always respected — Regardless of this setting, out-of-office events always block scheduling.