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Over 100 plain-language guides, written for working entertainers. Search, or browse by topic below. Still stuck? Reply to any Booked Solid email and a human answers.
Installing & updating
- Install Booked Solid on Windows (getting past the "Windows protected your PC" warning)
- The Mac download will not start, or the downloaded app will not open (including "my Mac is too old")
- Which version am I running - and why the app says "you're up to date" when it isn't (download and install the current app by hand)
- How updates work: the update badge and Restart & install
- Mac says the app cannot update: the "move the app" message explained
- Keeping Booked Solid awake: a spare computer, or your own VPS
- After an update my Mac asks for a password: the "booked-solid-app Safe Storage" prompt explained
- Install and update Booked Solid on Linux (AppImage, .deb and .rpm)
- Is there an iPhone app? Does it work offline? And what computer do I actually need?
- Downloading Booked Solid again: one installer per computer (there are no zip files any more)
Getting started
- Activate your license code and set up your account
- The autonomy dial: Show me, Check with me, or Run it
- First run: pick your BookingHQ workspace and get a first win
- Get Otto ready: the one-tap setup screen, and the Windows curl (35) / CRYPT_E_NO_REVOCATION_CHECK failure
- Bring your work over from another computer or your Claude chats
- Coming from the terminal version: your old commands in the new app
- Start here: from download to your first booking task, step by step
- Getting started with the DJ & AV edition
- Setting up the Skill edition in your own AI
- The terminal edition: where to get the current files, and which new features really work there
- "No BookingHQ found" when I point the app at the Booking HQ I built in the terminal
- How to reach support: live setup calls, group coaching, and reporting a problem (posts in the Facebook group never reach us)
- How does Booked Solid actually get me gigs? What to tell Otto on day one, with prompts to paste
Troubleshooting
- Sign in and fix a failed sign-in
- "Your license is paused" or license revoked - how to get back in
- Send us a support bundle: it is in Settings, not under "Help me"
- Grant microphone and screen permissions on Mac
- A Studio creation failed or did not produce a result
- "That license code was not found or is already in use": the three causes
- The app signed me out by itself: the honest reasons why
- Sign-in stuck or "on hold": when this computer cannot save your account
- "Your saved keys couldn't be unlocked on this machine": fixing keys after a computer change
- The app went blank or froze: how to recover without losing work
- Why Otto says browser control is not available
- "The app closed before the result was verified": why some jobs do not retry themselves
- Why the app uses more of your Claude plan than the terminal does - and what actually spends it
- Make Otto use the browser you're already signed in to (Edge or Chrome) - and stop "Verify you are human"
- Signed out of Claude: "Failed to authenticate", a 401, or "Login expired - please run /login" (including when it keeps coming back after a restart)
- I installed it and nothing happens: the app will not open, or the installer hangs and says "Application not responding"
- Booked Solid never asks me to sign in to Claude (and why Otto's own answer about it is wrong)
- Booked Solid has taken over Chrome on my Mac: extra windows, no new browser, and a Mac that will not restart
- The app pins my CPU and my Mac grinds to a halt (Intel Macs): the Performance settings that fix it
- Otto says "Upgrade to Max or Pro" or "your organization has disabled Claude subscription access" - but I already pay for Claude
- Otto says it doesn't have permission to open your browser on a Mac: the two halves you both need
- "The record could not be saved safely. Nothing was reported as completed" - I cannot save any gig edits
- I clicked "Review this decision" and nothing happened
- Otto opened its own browser window and wandered onto pages you didn't want
- A gig I closed, lost or finished still shows as due or overdue in Today
- Archiving a lead fails with an EPERM error: your Booking HQ is inside OneDrive
- Dozens of "Handle the Reply" cards piled up and the X won't dismiss them
- Mac says "no space left on device" but Finder shows terabytes free
- My antivirus flagged python.exe or a suspicious website - is that Booked Solid?
- A feature stopped working after an update: nothing was removed - check Connections first
- My due list is full of things that are not real leads (stray .md files in your Booking HQ)
- Can Otto write a draft inside Gmail using browser control? No - here's where your drafts actually go
- A run stopped before it finished and shows "Keep going": your Claude plan's usage window ran out
- My Claude plan drained overnight but Token history shows 0: where the usage really went
Plans & billing
- What your plan actually includes - and why a lifetime licence still says "Upgrade to schedule"
- Upgrading to Otto: there is no second licence key (and the stray Pearl key that landed at your other email)
- Buying Booked Solid OS: checkout, your license email, and activation
- Booked Solid OS vs KM Hub: which one is for you
- When a payment fails or you cancel: the license pause and renewal, start to finish
- I bought before the Kivi Media move: do I still own it for life, and who is the $100/month for?
- Refunds: who processes yours, and what happens if the original vendor already refunded you
Connectors
- Connect your accounts (Gmail, Calendar, Stripe, and the rest)
- Why an Anthropic API key on your computer switches off Gmail, Calendar and Drive
- Add email accounts and calendars (so gig dates never clash)
- Optional add-ons: integrations, Microsoft 365 sign-in, and Discover
- Run a private local AI with Ollama (free and offline)
- "Linked" or "couldn't confirm" doesn't mean broken: what each Connections badge means, and how to really test a connection
- Otto says Gmail isn't connected, but Connections shows it as Linked
- Set up Stripe deposit links safely with a restricted key
- The "Web browsing" switch will not turn on: update the app first, and the other reasons a connector refuses (key, sign-in, Node.js)
- Microsoft 365 by device code: what Otto can and cannot do in Outlook
- "The email server refused that sign-in" on a mailbox that isn't @gmail.com (your own domain, Hostinger, iCloud, Fastmail)
- Purpose tags on mail and calendars: bookings vs personal, and the clash check
- Most thorough, Balanced, or Fastest: what the thoroughness setting changes
- Let Otto browse the web with Chrome or Safari
- Computer control: let Otto work your desktop, and its limits
- Connect Microsoft 365 without an app password - and why a second account replaces the first
- "Check it" is green and the Gmail switch is on, but Otto still has no Gmail tools
- Email will not connect: antivirus mail shields (AVG, Avast, Norton)
- On a Mac, connections won't stick and I get a keyring error written for Linux
- Nothing in my Sent mail after Otto "sent" it: Otto only ever writes drafts
- Google Calendar or Drive shows Linked, but Otto keeps asking for an approval that never appears
- Google says app passwords aren't available for my account - even with 2-Step on
- Make clients see my own domain address instead of my personal Gmail
- Bring your Mago CRM in: the desktop connection, and the CSV route for terminal and Pearl
- Can I connect my own CRM? MCP servers for bringing data in, and the Lead Outbox webhook for pushing leads out
- I signed in to Microsoft 365 but no permissions screen appeared and the card never flipped
- Can Otto use my Apple Mail? No - here's what to connect instead
- Otto can read my email but can't save drafts: "Drafts folder doesn't exist"
- Otto can't find an email that's sitting right there in my Gmail
- Otto drafts from the wrong email: running several inboxes and personas at the same time
- There are two Email sections in the app - which one am I supposed to use?
- "Gmail isn't responding" right after I set up a new app password
- "You haven't granted permission to mcp__gmail__draft_email" - a second Gmail tool on your computer
- The app will not let me push to GitHub: the GitHub connection is look-only (and no app setting gates your git push)
- Autopilot says Gmail failed with "insufficient authentication scopes" (there are no Gmail scopes in this app)
- A 308 error when signing in to Mago (the terminal works fine): update the app
Otto features
- Set up the Booth: approve Otto from your phone (Otto only)
- Let Otto run on its own: scheduled tasks and self-starting Plays (Otto only)
- Auto-send: which touches can go out by themselves, and the caps that bound them
- Booth troubleshooting: approvals that ask for the desktop, and other quirks
- Can Otto make me an invoice? What he can write instead - and why asking burns so much
Using the app
- Use voice dictation: hold to talk anywhere in the app
- Set up watch folders and automatic backups
- The Studio: generate photos and video with your own Higgsfield account
- The top bar explained: updates, your phone, help, and the Advanced menu
- Where to find your past chats with Otto (it's now called Chat history)
- Task tabs: run several jobs side by side (Chat, Power view, Activity)
- The Help buddy: ask anything in plain words
- Notifications: what Booked Solid pings you about while it works
- Web browsing and Browser control: what Otto can and cannot do
- Watch folders: which dropped files come in and which are skipped
- What runs in the background while you are not looking
- Why the Studio needs a photo before it makes a video
- First-time voice dictation: setup and the common errors
- Drag and drop files into a task
Licensing & account
- Work offline: the 14-day grace and "Check again"
- Locked out: reset your password, or get a sign-in code (username or email both work now)
- Using Booked Solid OS on a second computer
- Sign out vs canceling: what Sign out actually does (and does not)
- Bought from the original Booked Solid vendor? Your old login still works
- My old Green Room link goes to the sales site: where the Green Room is now, and what happened to the old prompts
- I never got a license code: Pearl, Sol and terminal buyers, and what to do when the app asks for one
- Change the email address on your account (and the different way you swap a connected inbox)
- Can my VA or assistant run Booked Solid for me?
- Email me a sign-in code: get back in without a password (and what to do when no code arrives)
Privacy & data
Chat & tasks
- Chat with Otto: send, Forge this, and start fresh
- Ctrl+V does nothing in Power view: how to paste (and the build that fixed it)
- Queue messages while Otto is working
- Can I trust Otto's numbers? Where the app is exact, and where Otto can be wrong
- I pasted something and Otto ignored it: the "connect your PayPal" card that holds your message
- Otto said he'd "keep this queued" until a connection is back - will he actually pick it up?
Today, leads & inbox
- The Today tab: your daily briefing
- Gig Desk cards are blank, or a booked gig is stuck in "New Inquiries"
- The Tasks tab: everything queued, running, and done
- The Inbox: review drafted replies and send them yourself
- I already sent the draft myself, but the lead still says "review and send"
- A lead conversation went quiet and nothing flagged it: the three things that catch a reply you owe
- How to clear out old "Waiting on them" items and leads that are no longer live
- Leads I marked lost are still showing on my Calendar (and how to hide lead chips)
- Every lead says "0 of 6 facts" - even gigs I have already booked and been paid for
- Can replies go to a different address, and can the Inbox "Open" button use my own mail app?
- Cannot save a gig: This older record needs review and a field is longer than allowed
- "16 gigs need a quick fix": what the coral pill means and how to clear it
Activity & approvals
- The Activity screen: watch Otto work on the Board and Live views
- Decision cards: the Approve / Edit first / Chat about it buttons, why the text ends in "...", and "just so you know" notices that need no approval
- Otto changed or wiped out a file you wrote: undo the last run, and what to do when undo cannot help
- Second Look: the independent check after auto-acting plays
Plays & Autopilot
- Plays: every one-tap booking job explained
- Get set up recipes: one-tap 'Do it for me' setups
- Turn on Autopilot (Otto only)
- Fully Autonomous Booking: what it does and what always stays a draft
- Cold outreach in Booked Solid: what's built in (and what isn't)
- Scheduled tasks when the laptop was asleep or the app was closed
- Otto set the next follow-up for after the event date (how event-driven plays decide something is due)
- Why a play says it needs to learn something first
- "Blocked": the draft and file blocks explained (Google redirect links, overwriting a file in your Booking HQ, and the rename that gets it done)
- The DJ plays: No Dark Dates and Advance the Rider
- Why Autopilot turns itself off - and when turning off IS a fault
- A Play keeps looping and never writes anything (the Flywheel, the lead engine, Library Radar)
- What the morning run actually does - and why your Claude limit is gone before you start work
- School Radar and Library Radar: what they find, why they're US-only, and what the harvest sweep really does
- Nothing runs on its own any more: one stuck job can hold up every scheduled task
Dashboard & Brain
- The Dashboard: money in play, pipeline, and relationships (and where the Money in Motion numbers come from)
- The Brain: what's working, and approving Otto's proposed changes
- Using another memory tool alongside Otto (and why brain/ has to stay the only one)
- Running two different acts from one Booked Solid account - and which plan finds you leads
- Can I book for another entertainer as well as myself? What works today, and where the edges are
Settings & preferences
- Otto keeps using a line you told him never to use: make it a House Rule so it sticks
- Your Booking HQ folder: change it, find it, restore a backup, tune it up
- Places I listen: the social places Otto reads
- Make it yours: themes, your own colors, and language
- Set your aim: tell Otto what you're going for
- Sync your Mac's Contacts, Reminders, and Calendar
- The rest of the General tab: dynamic workflows, replay the opening, sign out, and more
- The access dropdown is greyed out for a tool you added yourself (and how far Settings > Permissions can really reach)
- Skills (Advanced): extra abilities Otto manages himself
- What automatic backups save, where they go, and why API keys are not inside
- Restoring a backup: the safety net and the "before restore" folder
- Set a floor rate that actually blocks low quotes
- How the do-not-contact list matches names (it blocks more than exact matches)
- Can I use Booked Solid in my language? Otto's language, the app's interface language, and what is still English
- What the app writes into my Booking HQ files (Deal stage, Next action due, and gate lines)
- Can Otto run on Grok, ChatGPT or Gemini instead of Claude?
- Where are the email templates? There aren't any, and here is where you actually change how your emails sound