Cumbersome Pro
Create, organize, and search Project files with AI
Keep drafts, reference documents, data, and code together in a Project. Cumbersome Pro lets you create and edit files yourself or with AI, organize them in folders, and ask questions across your files and past chats.
Organize a Project into folders
Open Project Files from a Project in the sidebar. Create nested folders, rename files and folders, and move them to another folder within the Project. File history stays with a file when you move it.
Ask the AI to use the same structure: "Create a Reports folder, then write a summary in Reports/summary.md." Its file tools work within the current Project.
Create files and review related AI edits
Write text, Markdown, HTML, code, or data files in the editor, or ask the AI to create them. New AI files and refinements during the response that creates them save automatically. Later AI edits and removals wait for your review.
Related pending changes from one AI response appear together. Open Review Changes, inspect the changes to each file, then choose Apply All or Discard All. Added and removed text is labeled in the comparison. A group that includes deletions identifies them before you apply it.
If a file changes outside the review, Cumbersome checks for a conflict before overwriting it. Apply All writes files in sequence, so an interruption or conflict can leave some changes applied and the rest awaiting review.
Recover drafts and earlier versions
Version History lets you inspect, export, and restore earlier saved work. Closing a manual edit without saving keeps a recovery draft on that device. Pending work stays available from chat and Project Files.
If Pro expires, you can still preview, share, export, and restore saved versions, or discard unfinished changes. Creating files, editing them in Cumbersome, and applying AI edits require an active subscription.
Search reference documents and past chats
Add PDFs, Word documents, supported text files, or images as reference material. Cumbersome extracts text and searches on your device. Your AI can read relevant passages without you attaching the same documents to each chat. Relevant excerpts are sent to the AI service you're using to answer the question.
Project documents are searchable independently of the Project's Conversation Search setting. Enable that setting to let the AI also find decisions and details from other chats in the same Project.
Answers can cite documents and conversations. A document link opens the current file, including after a rename; it can differ from the version the AI read. The conversation retains the original tool results.
File storage and sync
The default Project folder is in Cumbersome's iCloud Drive storage. Open Project Folder > Show in Finder on Mac, or Browse in Files on iPhone and iPad, to reach its named working files. You can edit them in another editor without exporting a separate copy. Outside additions, edits, moves, and removals appear in Project Files; Refresh Files rescans the folder when needed.
To use a folder you already have, start with an empty Project and choose Project Folder > Choose Existing Folder. Connecting a folder keeps its files at that location. Grant access to the folder separately on each device. Its sync and availability depend on where you keep it; Cumbersome does not copy it into the default iCloud folder.
Saved version history still uses Cumbersome's iCloud Drive storage, including when the working folder is elsewhere. Connecting an external folder does not remove that iCloud requirement.
What to know before you use it
- Folders, connected working directories, and grouped change review require Cumbersome 2.1 or later. Subscribe monthly or annually from Settings > About > View Pro Plans. AI provider usage is billed separately.
- The editor supports UTF-8 text files up to 1 MB. Reference imports support PDFs up to 50 MB and 300 pages, and other supported documents up to 25 MB.
- Opening HTML or code in Project Files displays its contents without running it. Renaming a file does not convert its format or rewrite links inside it.
- Deleting a file or folder permanently removes its contents and saved history after confirmation. Deleting the Project itself keeps its established working folder, but removes its saved history and drafts from Cumbersome.