Two shrouds down.
Watchkeeper was not designed in an office. It was built in the middle of the South Pacific, on a wounded boat, by a solo sailor who had just learned the hard way that he was the only person alive holding the information that could save him.
The passage that started it.
The plan was Easter Island. A lifetime dream, the most remote corner of the chart you can reasonably point a bow at, sitting at the far end of a two thousand mile line drawn from the Galapagos. Three days out from Rapa Nui, blowing 25 knots on the beam, two shrouds failed.
When your rig is deciding whether to stay standing, you do not get a committee meeting. Turning downwind unloaded the damaged side, which conveniently pointed the bow at the Gambier Islands instead. A length of Dyneema, a block and tackle, and fifteen minutes of work held the rig together. Rapa Nui was gone. The detour added two weeks to the leg, and meal planning aboard was about to get creative.
The part that changed everything.
Checking in with the shore crew taught two things fast. They had been sent into a panic, and if there had been real trouble they could not actually have helped much. Not for lack of caring. They simply did not have the information they needed. The position, the course, the intentions, the state of the boat and the state of the skipper all lived in exactly one place: one head, in the middle of the South Pacific.
The immediate fix was pure improvisation — some cobbled-together AI automation that emailed position and situation to the shore crew twice a day. Crude, but it worked. The panic ashore settled almost immediately. Not because the risk had changed, but because the people who cared finally knew what was happening and what to do if the messages ever stopped.
Two weeks is a long time to think. As a distraction from the food situation, it got built properly. That became Watchkeeper.
Who is behind it.
James Dunnigan left Victoria, British Columbia in September 2025 aboard Cloud Nine, at the start of a solo circumnavigation three years in the making. Down the coast to Mexico, a season in the Sea of Cortez, then the long legs south and west. La Paz to the Galapagos, with an equator crossing celebrated alone and, by the next morning’s account, perhaps a little too enthusiastically.
He holds an RYA Offshore Yachtmaster, spent his career building technology businesses, and works as a professional photographer, documenting the whole voyage at Cloud Nine Chronicles. Somewhere between Rapa Nui and the Gambier, those three threads braided themselves together.
What Watchkeeper does today.
Watchkeeper is an advanced online logbook and boat management platform built on a simple idea: good seamanship deserves good information.
The shore crew problem came first. Automated passage updates give the people ashore a real, living float plan. Where you are, how you are doing, where you are headed and when to worry. If the wheels ever come off, they hold the information a rescue coordinator would actually ask for.
Underneath that sits a proper digital logbook. Passages, watches, weather and engine hours quietly build themselves into a permanent record of your boat’s life. Around it all is boat management: maintenance schedules, systems and spares, the unglamorous discipline that keeps shrouds attached to boats.
Then there is the part every ocean cruiser learns to dread: paperwork. Watchkeeper keeps your ship’s papers organised by country, with current entry and exit tips for each one. Registration, insurance, clearance documents and crew documentation all live in one place, matched to the country in front of you. When you arrive somewhere new, you know what that country wants, and you have it ready. After a dozen clearances across the Pacific, that alone pays for the whole idea.
The philosophies of the Yachtmaster syllabus are baked into all of it. The software should serve seamanship, never replace it.
Where it goes next.
The roadmap is ambitious, and it is being tested the honest way, aboard a boat in the middle of an ocean. Hardware to connect the boat comes next, so Watchkeeper can read your instruments and systems directly instead of waiting for you to type. Native iOS and Android apps will put the logbook, the float plan and the ship’s papers in your pocket, ashore or offshore.
And then navigation. The goal is a future-forward take on what OpenCPN started: charting and passage tools built from the ground up on the technology available today, with AI doing the tedious work so the sailor can keep their eyes outside the boat.
Cloud Nine has been working west ever since the detour. Landfall at Rikitea after 3,300 hard miles, a season among the Gambier and the Australs, the Society Islands, and on toward Niue. The jury rig has long since been replaced. Watchkeeper stands its watch every day aboard this boat, and the shore crew now sleeps just fine.
The ocean will keep testing all of us. That is the deal we signed. But no sailor should be the only one holding the information that could save them.