I moved my small business Claude setup from local Cowork sessions to Claude Code cloud sessions. It's better, with caveats.

I'm a heavy Claude user. It's been a big help because I wear a lot of hats. I own/operate two small businesses, do consulting work, and volunteer my time as an admin for a non-profit. I'm not a developer and my computer expertise is nothing special. Over the past several months I built up a fairly heavy Claude setup on my home desktop: a folder of instructions and "recipes" for recurring jobs, a handful of custom skills, and 12+ scheduled tasks that run regularly. Most of it ran through Cowork on the desktop. Yesterday I moved almost everything to Claude Code cloud sessions and routines. Why I migrated • Local permission failures. Cloud cowork sessions were useless without the context of my local files. I could never get Dispatch to do what I wanted either; it seems dumber, doesn't consistently reply to me, and always seems to be missing permissions. • Scheduled tasks depended on the desktop. If my home machine slept or the power went out, the scheduled tasks would fail or hesitate because they couldn't access local files, even if the task was perfectly doable without the local folder. • I work from multiple devices. I wanted to start real work from my phone, laptop, or my dekstop at the office with full context. Very envious of the "/btw" command in particular. • Code seems more feature-rich. I occasionally see mentions on Reddit or in Anthropic blogs about people using commands that are not available in Cowork, but seem handy.\ • Timing. New Cowork sessions are moving to the cloud anyway, so I'd rather restructure on my own terms and understand how it works. Besides, I want to use the $250 in promo credit that Claude gave me for cloud sessions. How I migrated • I moved my local folder containing all of my instructions for Claude in a private GitHub repo. CLAUDE.md is now a short index, and the detailed recipes sit in subfolders that get read when needed. Every cloud session and routine clones it, so they all work from the same instructions. • I moved API keys out of local credential files into the cloud environment's credential settings. The proxy attaches them per host, so scripts never see a token. That's cleaner than what I had; despite instructions, Claude would occasionally put my API tokens in the transcript in plaintext. • I moved working files to Google Drive, with Reference / Inbox / Outputs subfolders. • I rebuilt my scheduled tasks as routines. Each routine prompt is two sentences in the same format: "You are running in a clone of [repo name]. Read [recipe for routine] and carry out its instructions." • Rather than editing skills, scheduled tasks, etc in the desktop app, Claude pushes changes to GitHub and I merge them. What's been great • Remote sessions finally work properly. Same context, same instructions, same credentials as the desktop. That was my primary motivation, and it works perfectly. • Migrating scheduled tasks to routines was seemless. I just got Claude to tell me how to migrate it. It was manual but simple. What has been painful • Auto-mode permissions are worse in Claude Code. This one surprised me. When a scheduled task in Cowork needed a permission, I had the option for "Allow once" or "Always allow for this task". I'm not seeing an "Always allow" option in routines. I'm sure there's a workaround, but I didn't expect that feature to be missing. • Files on the cloud is not as seamless as I expected. Editing files remotely seems clunky. I'm running into this frequently with XLSX files stored in Drive. Unless you want to spend a ton of tokens, the workflow seems to be to download the file, edit it, and re-upload it. The official Drive MCP connector doesn't support replacing files, but the Composio connector does, so that's what I'm doing for now. I'll probably have to convert my Excel sheets into Google Sheets in the future. Caveats • This project took time. The migration (including the planning) maxed out three 5-hour sessions on my Max 5x plan using Fable 5.1 spinning up Opus 5.5 subagents. • I still need local sessions for some work. I haven't figured out a good way to handle image rendering or video editing in a cloud environment yet. Anything with large files For now, those are still running as local sessions. Bottom line If you regularly work across multiple devices, the migration is worth it.