Wispr Flow

Most of what I put into Claude Code is dictated rather than typed. For 11 months that ran through Wispr Flow on a Windows laptop, with the Flow keyboard on my iPhone as well. You press a shortcut, talk, and the text lands in whatever app the cursor is in, including a terminal. I built up my own dictionary of tool names, brand names and place names, and once a word was in there it mostly came out right. On Windows it worked every day for the full 11 months without failing once.

The iPhone app was a different story. On 18 December 2025, on version 1.29, every transcription failed when I finished talking. I had to open the Flow app and retry each one by hand. Support confirmed a transcription problem on iPhone the same day and shipped a fix in version 1.30 the next day. Ten days later, on version 1.32, it was failing every time again. That ticket got a holiday auto-reply, then an AI support agent, then a person on 2 January with the standard steps: check the network, restart the app, reinstall it.

I cancelled on 25 September 2026, and the reason was not a fault. Handy is free, open source, and transcribes on my own laptop, so no audio leaves the machine. It is less accurate on names than Wispr Flow, and that is the one thing I miss. But most of what I dictate is read by Claude, and Claude works out what I meant even when a word comes out wrong. Once that was true, US$180 a year bought me very little. If most of what you dictate is read by people, not an AI, the name accuracy is worth more and the maths changes. On the phone I now use the iPhone's built-in dictation.

A few facts that are easy to miss on the pricing page. The free plan allows 2,000 words a week on desktop, which is under 300 words a day, and limited use on mobile. Pro removes the limit for US$15 a month, or US$12 a month on yearly billing. Students and educators get 50% off Pro. Transcription always runs on Wispr's servers, so Flow needs an internet connection and your audio leaves your device. Two privacy settings are on by default: one lets Wispr use your dictations to improve its models, and one stores your transcripts and audio on its servers. Both are under Settings, then Data and Privacy. Last, uninstalling the app does not stop the charge. You cancel under Plan and Billing.