Five things hold the Start sync button and two of them explain nothing on screen. How to find which one it is.
Something on the page isn't finished yet, and the button waits for it. Five different things can hold it, and only one of them is a plan limit.
The button sits at the bottom right of the sync composer and says Start sync. (There's no longer a Continue button — the composer used to be two steps and is now one screen.)
1. The sync has no name. The name field is near the bottom, under Sync details. It fills in automatically from the calendars you picked, but if you cleared it, or typed spaces, the button stays off. There's a red line under the settings saying so.
2. You picked a custom title and left the text empty. Under Appearance, if the title is set to Replace title or Add a prefix, the text box next to it can't be blank. Type something, or switch the title back to Title says "Busy" or Use original title.
3. An exclusion rule has no value. Under Filters, a "Title contains" rule you added but never typed into blocks the button. Type the word you want to skip, or remove the row.
4. The setup is over one of your plan's limits. This is the one with a message attached — a banner appears above the button naming the limit you hit. Four different limits can produce it:
The last one is why a setup can be refused while you're still under the calendar count.
5. It's already starting. The button reads "Starting…" for a moment after you click. Nothing is wrong.
The settings only show up once your calendar picks make a workable sync. Before that there's a line telling you what's missing:
You've picked an iCal or ICS feed subscription. Those are read-only — nothing can write to them — so a sync containing one can only be a Push, with the feed as the source. No plan unlocks this. If you want two-way sync with iCloud, connect it as a CalDAV account rather than subscribing to its ICS link.
Switching to Mirror anyway is allowed; it drops the read-only calendars from the selection and tells you how many it removed.
Two reasons, and they look identical until you click.
Another sync already covers this pair. Two syncs writing the same direction between the same two calendars is how you get duplicates, so the second one is refused. Clicking the dimmed row opens a panel naming the sync that already owns it, so you can edit that one instead of building a second.
The account needs reconnecting. That row is properly disabled and won't respond. Reconnect the account under Accounts first.
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Still stuck? Support will read your actual setup and tell you what it sees — describe what you expected and what you got.