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TroubleshootingGoogle CalendarOutlookCalendar hygiene

A double booking just happened. Here is how to find out why, and stop the next one

A step-by-step diagnosis for clashes across Google Calendar and Outlook: which calendar held the conflict, how it was marked, and the specific fix for each cause, plus a ten-minute monthly calendar check.

When two appointments land on top of each other, the instinct is to apologise, move one and carry on. The trouble is that the same gap will produce the same clash again next week. A double booking is a symptom, and nearly every one traces back to a small number of causes: a calendar that was never connected, an event marked as free, an all-day entry, a shared or delegated calendar, a time zone slip, a sync that had not caught up, or a booking that never went through the booking page at all.

This guide is a troubleshooting flow. Start with the clash in front of you, work through the questions in order and you will usually find the cause within a few minutes. If you want the background on how free/busy checking works first, read how calendar sync prevents double bookings, then come back here when something goes wrong.

Working backwards from the clash

Open both clashing entries side by side before you change anything. Moving or deleting one of them first destroys the evidence. Then work through these questions in order. Most clashes are explained by the first three.

Question 1: Which calendar held the clashing event?

Look at the entry that was already there when the booking came in. Note the account (Google or Microsoft), the calendar name and the colour. Then check your booking tool's connected calendars list. If that calendar is not on the list of calendars checked for conflicts, you have found the cause. This is the most common one, especially with second Google calendars ('Family', 'Clinic', 'Site visits'), a work Outlook account added after you set up, or a calendar someone else shared with you.

Fix: connect the account if it is not connected, then tick that specific calendar for conflict checking. Calenix connects Google Calendar and Microsoft Outlook. The Free plan includes one connected calendar and the Individual plan up to six, so if you have run out of connections, either upgrade or consolidate commitments into a calendar that is already checked. Our guides to syncing your booking calendar with Google Calendar and connecting Outlook to your booking page walk through the settings.

Question 2: Was the event marked busy?

Open the clashing event and look at its availability setting. In Google Calendar it shows as Busy or Free. In Outlook it is 'Show as' with Free, Working elsewhere, Tentative, Busy or Away. Conflict checks generally read free/busy status, so an event marked Free is treated as open time. Invitations you accepted from other people, webinars and reminders you set up years ago are frequent culprits, as are tentative replies.

Fix: change the event to Busy. If it repeats, change the whole series, not just this occurrence. Decide once how you treat tentative holds and apply it consistently.

Question 3: Was it an all-day event?

All-day entries are often created as Free by default, because people use them for notes such as 'Mum's birthday' or 'Invoice day'. If you used one to mark leave, a conference or a site day, it may not have blocked anything.

Fix: set all-day entries that mean 'unavailable' to Busy, or replace them with a timed event covering your working hours.

Question 4: Was it private, delegated or on someone else's calendar?

Private events normally still count as busy for free/busy purposes; the title is hidden, not the time. Problems start with delegated and shared calendars. If an assistant or colleague adds an appointment to a shared team calendar, or to your calendar through delegate access in a way that lands on a calendar you have not connected, your booking page never sees it.

Fix: agree which calendar delegates must write to, and make sure that calendar is checked for conflicts. If a shared calendar holds many people's events, do not connect it as your conflict calendar, or everyone else's appointments will block your time. Ask for your entries to be added to your own calendar instead.

Question 5: Do the times match once time zones are applied?

Compare the start times in both systems. A one-hour difference is the giveaway. Common sources are a booking tool set to the wrong home time zone, an event created while travelling, a calendar whose own time zone setting differs from your device, and daylight saving changes in the UK (late March and late October) or in parts of Australia (early October and early April). Our guide to scheduling meetings across time zones covers the offsets.

Fix: set your time zone by city in Calenix and in each calendar, and check events created during travel.

Question 6: When was each entry created?

Check the creation or invitation time on both. If the personal event was added only a minute or two before the client booked, or two people booked the same slot almost at once, you are looking at a timing gap: calendar changes do not always reach a booking tool instantly.

Fix: add personal commitments as early as you can, and avoid making last-minute changes to your diary during busy booking periods. If this cause repeats often, it is worth asking support how quickly your connected calendars refresh.

Question 7: Did the booking come through the booking page?

If one of the two appointments was typed straight into a calendar after a phone call, a text or a chat at the door, and the other came through the booking page, the question is which arrived second. A booking tool cannot block a time that was only promised verbally, or written in a paper diary or an unconnected calendar.

Fix: make the booking page the route for every booking, including the ones you take by phone. You can open your own page and book on the client's behalf.

Bonus: the calendar you cannot connect

Apple iCloud Calendar is not a Calenix integration. If a clash came from an iCloud calendar, either move those commitments into Google or Outlook and view them on your iPhone, or copy key dates across as busy blocks. Our page on Apple Calendar and online appointment scheduling explains the workaround.

Why a diagnosis beats a quick apology

Each double booking costs more than the slot. Someone is told their appointment has moved, a client sits in a waiting room, or you join a call ten minutes late from another meeting. Clients forgive one clash. A second one, especially for the same client, starts to look like disorganisation.

Fixing the immediate clash without finding the cause means you are relying on luck. Most causes are structural: a calendar not connected, a habit of accepting invitations as free, or a staff member who writes in the wrong calendar. They do not go away on their own, and they tend to get worse as you add calendars, staff or clients in other time zones.

A short, repeatable diagnosis also changes how a team talks about mistakes. Instead of 'who booked over me?', the question becomes 'which of the seven causes was it?'. That keeps the conversation on the system, not the person, and the fix usually takes less than five minutes once you know where to look.

Finally, the record of causes is useful in itself. If three of your last four clashes came from one shared calendar or one booking channel, that tells you where to put effort. If you run both a Google and an Outlook diary, our guide on scheduling across Google Calendar and Outlook is a good next read.

What a proper diagnosis gives you

A named cause: you know whether it was a connection, a status, a time zone or a channel problem.

A fix that sticks: changing the right setting stops the same clash coming back next week.

Less blame: the team discusses the calendar setup rather than whoever took the booking.

Fewer surprises after changes: you know what to recheck when a calendar or account is added.

Cleaner calendars: busy and free statuses start to reflect what you actually do.

Client confidence: fewer apologetic emails moving appointments at short notice.

The double-booking diagnosis in 7 steps

1

Freeze the evidence — Before moving anything, open both entries and screenshot or note the calendar, account, status, time zone and creation time of each.

2

Trace the clashing calendar — Find which account and calendar held the earlier entry and check whether it appears in your booking tool's list of calendars checked for conflicts.

3

Check status and event type — Look for Free, Tentative or Working elsewhere statuses, all-day entries and repeating events where only one occurrence was changed.

4

Compare time zones — Line up the start time in the booking tool, each calendar and the client's confirmation. A one-hour gap points to a time zone or daylight saving issue.

5

Find how each booking arrived — Ask whether either appointment was added directly by you, a colleague or a delegate rather than through the booking page.

6

Apply the matching fix — Connect or tick the missing calendar, correct the status, set the right time zone or move the booking channel onto the booking page.

7

Test and log it — Create a test busy event in the affected calendar, confirm the slot disappears from your booking page, then note the cause in a simple log.

Symptom, likely cause and fix

FeatureLikely causeWhere to checkFix
Clash with an event you can see on your phoneCalendar not connected or not tickedBooking tool's connected calendars listConnect it and enable conflict checking
Clash with an accepted invitationEvent marked Free or TentativeEvent's Busy/Free or 'Show as' settingSet to Busy, for the whole series
Booked on a day you were on leaveAll-day entry set to FreeThe all-day event's statusMark Busy or use a timed block
Clash with something an assistant addedDelegate wrote to an unchecked calendarWhich calendar the event sits inAgree one target calendar and check it
Times one hour apart in different placesTime zone or daylight saving mismatchTime zone in tool, calendar and deviceSet every tool to your city
Event added minutes before the bookingSync timing gapCreation times of both entriesAdd commitments earlier; ask support about refresh timing
Phone booking clashes with online bookingBooking taken outside the systemHow each appointment was createdBook every appointment through the page

The monthly calendar hygiene check

Once a month, compare the calendars on your phone with the list of calendars your booking tool checks, and close any gap.

Filter for events marked Free or Tentative in the coming month and correct any that actually mean you are unavailable.

Scan the next four weeks for all-day entries and make sure leave, conferences and site days are set to Busy.

Check the time zone in your booking tool, each calendar and your devices, especially in the weeks around daylight saving changes.

Ask anyone with delegate or shared access which calendar they have been writing to, and confirm it is still checked.

Review your clash log: if one cause appears twice, fix the underlying habit rather than the individual events.

After the check, book a test appointment on your own page and cancel it, so you know the whole path still works.

Mistakes that make clashes harder to trace

Deleting or moving one of the clashing entries before noting where it lived and how it was marked.

Connecting a busy shared team calendar as your conflict calendar, so colleagues' appointments block your slots.

Fixing one occurrence of a repeating event instead of the whole series, so the clash returns next week.

Assuming an iCloud calendar is being checked because it appears alongside your Google calendars on your iPhone.

Blaming the booking tool for a clash caused by an appointment that was only ever written in a paper diary.

Skipping a test after adding a new account, calendar or staff delegate.

Example: two clashes at an osteopathy practice in Cambridge

A fictional two-osteopath practice in Cambridge takes most bookings online for 45-minute treatments. Each osteopath has a booking page on Calenix. In early October 2026 they had two clashes in a week and ran the diagnosis on both.

Clash 1: Tuesday 13 October, 10:30

A new patient booked online at 10:30, but the osteopath was already on a home visit. The home visit had been added by the part-time receptionist to a shared Google calendar called 'Practice visits'. That calendar was visible on everyone's phone but was not connected for conflict checking. Cause: calendar not connected. Fix: rather than connect the shared calendar, which would have blocked both osteopaths for every visit, they agreed the receptionist would add each visit to the treating osteopath's own Google Calendar, which was already checked.

Clash 2: Thursday 15 October, 14:00

A follow-up patient booked into a slot during an online CPD session. The CPD invitation had arrived in the osteopath's Outlook account and had been accepted as Tentative. Outlook was connected, but tentative events were not blocking time. Cause: event status. Fix: change the series to Busy and adopt a simple rule: anything you intend to attend is Busy.

The second osteopath also had a personal Google calendar and an Outlook account from teaching work, so she needed three connected calendars. That took her beyond the Free plan's single connection, so she moved to the Individual plan, which allows up to six.

The illustrative maths: if each clash costs one 45-minute treatment at £55 because a patient has to be rebooked or does not return, two clashes a month is £110, or £1,320 a year, before counting the time spent apologising. A ten-minute monthly check is a cheap way to protect that.

FAQ

Frequently asked questions

Fewer clashes

Connect the calendars that hold your real commitments

Start free with one connected Google or Outlook calendar and a booking page that hides busy times. Move to Individual when you need up to six calendars checked. No card needed.