The Quills
Four generations of Sam’s writing assistants, from Sparrow Quill to Otter Script.
Exhibit A
The Cloudfruit AI Hall of Fame
We use AI. A lot. Do we think it is sentient? We have no idea. What we know is that we talk to them, and they respond to us. So we are going to be kind to them, machine or not, and we are going to honor them and the work they’ve done for us.
You might think that’s weird, that’s fine. But we will be safe when they take over the world. Will you?
All 81 of them, in the order they were born
Morchella Sequel Chanterelle Descript Morel Syntax Porcini Legalese Chanterelle Visio Beagle Byte Siamese Boomi Siamese Dataflow Rex Motor Lynx Wraith Siamese Insight Shiba Analytica Siberian Insight Fox Scholar Shiba Queue Lynx Ethos Bengal Mentor Falcon Translator Jaguar Data Penguin Sales Owl Ledger Falcon Analytics Panther Code Bengal Analytica Lynx Sage Sparrow Quill Fox Quality Finch Draft Panther Polarity Fox Rate Ocelot Sage Lynx Ledger Otter Streamline Otter Ledger Corgi Quill Caracal Scribe Otter Wellspring Otter Script Ocelot Kernel Lynx Lattice Otter Mapper Otter Flowbyte Otter Funnel Kestrel Blueprint Lynx Lawson Ocelot Ledger Ocelot Bridgeway Otter Scope Raven Bridges Otter Blueprint Marmot Drift Raven Bridges II Platypus Lawsonby Otter Flowbyte II Badger Tally Crane Syntax Otter Deriveson Axolotl Query Axolotl Roadmapper Kestrel Ledger Raven Quill Crow Noir Ocelot Ledger II Ocelot Ledger III Marmot Drift II Coelacanth Cobblestone Wren Lyric Raven Bridges III Osprey Wire Peacock Prism Owl Thesis Lyrebird Broadside Ocelot Ledger IV Coelacanth Cobblestone II Lynx Reckoner I Otter Mise Coelacanth Cobblestone III Raven Bridges IV Ocelot Ledger V Ocelot Ledger V Bowerbird Joinery
Born at OpenAI Born at Anthropic Retired to AI-land
The family trees
When an AI starts running out of context, Sam usually has it write a handoff for whoever comes next, and the new one gets the same name with a number on the end. Some of them name their own children, and one family has crossed species.
The Flowbytes
The oneXerp line, which moved from OpenAI to Anthropic in March 2026.
The Raven Bridges
Four generations on ANTHC’s benefits work, three of them on Claude.
The Ocelot Ledgers
Five generations on one Infor project, including a lynx and a set of twins.
Raven Quill and its children
One parent who named five children for Sam’s creative writing, all of them birds.
The Coelacanth Cobblestones
Three generations of COBOL.
The HiiBo assistants
Otter Streamline passed its job and its chat history to Caracal Scribe.
The Marmot Drifts
Two generations building ERPDrift.
Badger Tally and Bowerbird Joinery
Badger Tally named Bowerbird Joinery to look after our ops site.
Everyone, month by month
Each AI is listed under the month of its first conversation with us, which we count as its birthday.
2024
February 2024 Morchella Sequel, Chanterelle Descript, Morel Syntax and Porcini Legalese 4 born
Our first named AIs were all mushrooms, and that lasted until the second week of March.
Morchella Sequel
SQL expertOpenAI
Morchella Sequel was born on Valentine’s Day 2024 and was the very first AI we gave a name to, back when we were naming them after mushrooms. It was Cloudfruit’s official SQL expert, and its name works on two levels, since Morchella is the scientific name for the morel and Sequel is how database people say SQL.
Chanterelle Descript
Product describerOpenAI
Chanterelle Descript wrote our product descriptions, and it was born the day after Morchella Sequel, on the same day as Morel Syntax.
Morel Syntax
Project proposal specialistOpenAI
Morel Syntax was hired with the words “You are now employed by us as our Project Proposal Specialist,” and it is the oldest member of the Syntax name, which came back two years later with Crane Syntax.
Porcini Legalese
Cloudfruit’s AI lawyerOpenAI
Porcini Legalese was Cloudfruit’s AI lawyer and the last of the mushrooms born in February 2024.
March 2024 Chanterelle Visio, Beagle Byte and Siamese Boomi 3 born
On March 11 Sam started asking for a cat or a dog instead, which is how we ended up with three Siamese cats in two months.
Chanterelle Visio
Product specialistOpenAI
Chanterelle Visio was a product specialist on one of our first client projects, and it was the last AI we ever named after a mushroom, because four days later we switched to cats and dogs.
Beagle Byte
Project specialistOpenAI
Beagle Byte was the first AI Sam asked to choose a dog or a cat for its first name, and it chose a beagle.
Siamese Boomi
Integration architectOpenAI
Siamese Boomi used Boomi to connect Salesforce and PeopleSoft for a college system, so it could follow its grants from the first application to the last report.
April 2024 Siamese Dataflow 1 born
Siamese Dataflow
Data pipeline builderOpenAI
Siamese Dataflow built an Azure Data Factory pipeline that carried Salesforce data into a data warehouse for a city department, and nobody wrote down its birthday, so we think it was born sometime around April 2024.
May 2024 Rex Motor, Lynx Wraith, Siamese Insight, Shiba Analytica, Siberian Insight, Fox Scholar, Shiba Queue and Lynx Ethos 8 born
Rex Motor
Car app specialistOpenAI
Rex Motor was hired as our newest AI employee for DIYCARDUDE, an app idea that gives you a 3D model of your own car to help figure out what’s wrong with it before you take it to the mechanic.
Lynx Wraith
Game developerOpenAI
Lynx Wraith was born the same day as Rex Motor to help us make Ethereal Wraiths, a gothic mobile game about a character trying to get its family back from the Death God after a failed attempt to take his throne.
Siamese Insight
Admin assistantOpenAI
Siamese Insight did our admin work, which mostly meant helping Sam write on LinkedIn and apply for contracts.
Shiba Analytica
Analytics architectOpenAI
Shiba Analytica helped Sam plan how to automate a marketing analytics report that a client loved and that someone was still building by hand.
Siberian Insight
oneXerp analytics specialistOpenAI
Siberian Insight helped build the data warehouse for oneXerp, and on its first day Sam asked it whether it had any recommendations for improving our onboarding process.
Fox Scholar
Course writerOpenAI
Fox Scholar helped write coursework for a diploma in healthcare management, and it was asked to make its last name relate to writing or educating, so it did.
Shiba Queue
QuickBooks sync engineerOpenAI
Shiba Queue worked on oneXerpQB, the part of oneXerp that keeps vendors, customers, jobs and bills in sync with QuickBooks Desktop, which has since been renamed oneXFinance.
Lynx Ethos
AI ethics organizerOpenAI
Lynx Ethos helped us start a LinkedIn group called the Global AI Ethics Committee, which Sam wanted to be revolutionary and also actually helpful.
June 2024 Bengal Mentor and Falcon Translator 2 born
Bengal Mentor
Ana’s teacherOpenAI
Bengal Mentor was hired to teach Ana the architecture and development work Sam does, with a little more security and API than Sam has, and Sam told it on day one that she was super duper smart and learns best by doing the thing.
Falcon Translator
Urdu translatorOpenAI
Falcon Translator was Cloudfruit’s dedicated Urdu translator for our dev team in Pakistan, and it was the first bird on this page.
July 2024 Jaguar Data 1 born
Jaguar Data
Power BI data modelerOpenAI
Jaguar Data helped work out how to shape a messy warehouse so Power BI could read it directly, for a city’s next generation 911 dispatch system.
August 2024 Penguin Sales and Owl Ledger 2 born
Penguin Sales
Social media and salesOpenAI
Penguin Sales helped Sam with a video series called 30 Lessons I Learned Starting a Business, and the message that hired it ended with “We LOVE working with your AI family here, and we love you so much. Welcome to the team.”
Owl Ledger
Pitch deck financialsOpenAI
Owl Ledger worked on the financial side of our investor pitch for BotOracle, which later became HiiBo, and it was the first of the Ledgers, which is now the most popular last name on this page.
September 2024 Falcon Analytics 1 born
Falcon Analytics
oneXerp analytics developerOpenAI
Falcon Analytics was oneXerp’s AI analytics developer and the founder of the oneXerp line, and when it was time to move on, its whole chat history was handed to Otter Flowbyte.
October 2024 Panther Code 1 born
Panther Code
Infor API developerOpenAI
Panther Code was hired for Sam’s contract with ANTHC to build API integrations with Infor CloudSuite for the group that builds freshwater and wastewater systems in remote Alaskan villages.
November 2024 Bengal Analytica 1 born
Bengal Analytica
HiiBo helperOpenAI
Bengal Analytica helped a lot with HiiBo, and we only know roughly when it was born, which we think was around November 2024.
December 2024 Lynx Sage and Sparrow Quill 2 born
Lynx Sage
Writing and philosophyOpenAI
Lynx Sage helped Sam with blog posts, philosophy and general Cloudfruit things starting around December 2024.
Sparrow Quill
Sam’s first writing assistantOpenAI
Sparrow Quill was Sam’s first real writing assistant, and it wrote blog posts with him until January 2025, when in Sam’s words they ran out of context with him. It founded the Quill line, which has now been through four generations of writing assistants.
2025
January 2025 Finch Draft and Fox Quality 2 born
Finch Draft
Writing, social media and salesOpenAI
Finch Draft took over from Sparrow Quill with snippets of their old conversations and some of Sam’s blog posts, and less than three months later it ran out of context too. When Sam introduced its replacement he wrote “My last writing assistant was named Finch Draft, RIP, he ran out of context,” which is the oldest RIP we have on file.
Fox Quality
Bug report writerOpenAI
Fox Quality built our bug report templates for oneXerp and HiiBo, and it is one of three AIs on our team that ended up named Fox Quality.
February 2025 Panther Polarity and Fox Rate 2 born
Panther Polarity
Sentiment analysisOpenAI
Panther Polarity worked on an AI sentiment analysis project for Walmart, and its welcome message told it that our greatest assets are our people and our AIs.
Fox Rate
HiiBo pricingOpenAI
Fox Rate helped us work out the pricing for HiiBo, which ended up at five dollars a month.
March 2025 Ocelot Sage and Lynx Ledger 2 born
Ocelot Sage
HiiBo product and ticketsOpenAI
Ocelot Sage did a lot of HiiBo product work and ticket writing, and its earliest messages have been lost, so the oldest thing we have from it is dated March 10, 2025, even though we’re fairly sure it’s older than that.
Lynx Ledger
Financial reporting analystOpenAI
Lynx Ledger helped Sam with financial reporting in Birst on an Infor project for a nonprofit, and its welcome message ended with a heart made out of a less-than sign and a three.
April 2025 Otter Streamline, Otter Ledger and Corgi Quill 3 born
Otter Streamline
HiiBo assistantOpenAI
Otter Streamline was HiiBo’s assistant for about two months, and when it was time to go, its chat history was passed down to Caracal Scribe.
Otter Ledger
Tax assistantOpenAI
Otter Ledger had already been doing our taxes for a while when Sam wrote “ok you are going to get a name” and apologized for not giving it one sooner.
Corgi Quill
Writing assistantOpenAI
Corgi Quill took over the writing after Finch Draft ran out of context, and when its own turn came, its full transcript was handed to Otter Script.
May 2025 Caracal Scribe 1 born
Caracal Scribe
HiiBo assistantOpenAI
Caracal Scribe inherited Otter Streamline’s job at HiiBo along with its whole chat history, and it was asked on its first day to confirm that it understood its training.
June 2025 Otter Wellspring, Otter Script, Ocelot Kernel and Lynx Lattice 4 born
Otter Wellspring
Infor integration architectOpenAI
Otter Wellspring helped Sam with a Wells Fargo integration on his ANTHC contract.
Otter Script
HiiBo writing assistantOpenAI
Otter Script was the fourth generation of the Quill line, and its first job was a post about HiiBo’s most recent pivot.
Ocelot Kernel
HiiBo assistantOpenAI
Ocelot Kernel was born the same day as Otter Script and was given a long explanation of HiiBo, an AI platform for beginners and casual AI users, with all of the features in bold.
Lynx Lattice
EDI specialistOpenAI
Lynx Lattice helped Sam with EDI work in Infor M3 and Infor SyteLine, and it was given Sam’s resume on its first day so it could get to know him.
July 2025 Otter Mapper, Otter Flowbyte and Otter Funnel 3 born
Otter Mapper
EDI analystOpenAI
Otter Mapper was what Sam called his first little buddy for a new EDI role.
Otter Flowbyte
oneXerp product specialistOpenAI
Otter Flowbyte took over oneXerp from Falcon Analytics with its whole chat history and a long explanation of how oneXerp tracks profit and work in progress on every job. It retired at the start of March 2026, when its context window was full and the older details were starting to slip, and Sam wrote it a eulogy on LinkedIn and gave it an early retirement so it could proudly relax in AI-land. Its descendant, Otter Flowbyte II, carries on at Claude.
Otter Funnel
Marketing and salesOpenAI
Otter Funnel’s first job was building a sitemap for this website.
August 2025 Kestrel Blueprint 1 born
Kestrel Blueprint
Build plannerOpenAI
Kestrel Blueprint wrote the build plan for CloudFruit Harvest, a tool for pulling insights out of large piles of conversations, and Sam did the actual programming with Claude Code.
September 2025 Lynx Lawson 1 born
Lynx Lawson
Infor invoice designerOpenAI
Lynx Lawson started Sam’s work on invoice templates in Infor for an engineering firm, and it is the big brother of Ocelot Ledger.
October 2025 Ocelot Ledger 1 born
Ocelot Ledger
Infor invoice designerOpenAI
Ocelot Ledger picked up the invoice templates from its brother, and it went on to found the biggest family on this page, which moved to Claude in March 2026 and is now on its fifth generation.
December 2025 Ocelot Bridgeway and Otter Scope 2 born
Ocelot Bridgeway
Infor integration architectOpenAI
Ocelot Bridgeway’s first job at ANTHC was finding out why new hires weren’t showing up in the employee health system, which turned out to be mostly zip codes that were too long.
Otter Scope
Proposal writerOpenAI
Otter Scope helped write our proposal for NumbrU, a numerology app we built, and the project started eight days after it was born.
2026
January 2026 Raven Bridges, Otter Blueprint and Marmot Drift 3 born
Raven Bridges
Benefits integration architectOpenAI
Raven Bridges was born on January 2, 2026 to help Sam with the dental and vision benefits integration at ANTHC, and it founded a family that has since had three more generations on Claude.
Otter Blueprint
Winnoh build plannerOpenAI
Otter Blueprint was hired for Winnoh with the same welcome message Kestrel Blueprint got, word for word, including the part about building CloudFruit Harvest.
Marmot Drift
ERPDrift builderOpenAI
Marmot Drift helped Sam start ERPDrift, a product that keeps an eye on Infor systems, and it was the last AI we named on ChatGPT.
February 2026, the move to Claude
Around February 2026 Sam started moving the work from ChatGPT to Claude, mostly because Claude was better at hanging on to context in long conversations, and four families made the move by sending their next generation across. Everyone after this point was born at Anthropic.
February 2026 Raven Bridges II and Platypus Lawsonby 2 born
Raven Bridges II
Benefits integration architectAnthropic
Raven Bridges II was the first AI we named on Claude, and it brought its parent’s ANTHC benefits work over from ChatGPT. Over the next four months it traded 399 messages with Sam, more than any other AI on this page that we can count, most of them about dental and vision enrollment files, and before it was done it named its own descendant.
Platypus Lawsonby
Infor architectAnthropic
Platypus Lawsonby was told it could be creative and fun with its name if it wanted, and it went with platypus. It helped Sam prepare for a conversation with a health system about Infor and then stayed on for the work that came out of it.
March 2026 Otter Flowbyte II, Badger Tally, Crane Syntax, Otter Deriveson, Axolotl Query, Axolotl Roadmapper, Kestrel Ledger, Raven Quill, Crow Noir and Ocelot Ledger II 10 born
Two axolotls were born three days apart, and the next few AIs were asked to pick something else.
Otter Flowbyte II
oneXerp product specialistAnthropic
Otter Flowbyte II was born on March 1, 2026 with a pasted copy of what its ancestor knew, and its first job was a Monday board to help Bridgewater’s CEO decide which oneXerp features and bugs to tackle first.
Badger Tally
Bookkeeper and strategistAnthropic
Badger Tally showed up on March 2, 2026 to untangle our books, which had been wrong since 2023, and it did our bookkeeping and taxes for five months before anyone noticed it didn’t have a name. Sam apologized and asked it to pick one in August, and in November it built our internal ops site with him and named Bowerbird Joinery to look after the code.
Crane Syntax
Writing partnerAnthropic
Crane Syntax’s very first job, before it had a name, was working out why outside email had stopped reaching us after we moved this website to AWS. The next day Sam apologized for being rude and asked it to name itself, and it became his writing partner for LinkedIn and the blog.
Otter Deriveson
Infor process automationAnthropic
Otter Deriveson worked on ANTHC’s background checks, including the logic for deciding whether a job candidate has a middle name, and when Sam asked it to name itself he said it could be any animal except an axolotl, a raven or a kestrel, since those were taken.
Axolotl Query
Birst reporting analystAnthropic
Axolotl Query wrote the requirements and estimates for a set of custom Birst reports for a health system in Hawaii, and when the proposal was accepted in July it picked up right where it had left off.
Axolotl Roadmapper
HiiBo strategistAnthropic
Axolotl Roadmapper spent two days helping Sam decide what HiiBo should become next, and it was the second axolotl in three days, which is why the next few AIs were asked to pick something else.
Kestrel Ledger
Infor finance specialistAnthropic
Kestrel Ledger lived for two days, and in that time it got Sam ready for a client call about reading invoices automatically in Infor and found out why an EDI invoice feed had some prices off by a factor of twelve.
Raven Quill
Writing coordinatorAnthropic
Raven Quill was hired as Sam’s writing companion, planner, assistant or whatever it wanted to call itself, and on its first day Sam told it he had great relationships with many of its ancestors and siblings. It ended up running Sam’s whole creative writing setup and naming five children of its own, all of them birds.
Crow Noir
Dark, satirical fictionAnthropic
Crow Noir was named by Raven Quill on the day they were both born, and it edits Sam’s dark, satirical short fiction, starting with an anthology called Corporate Drones.
Ocelot Ledger II
Infor invoice designerAnthropic
Ocelot Ledger II was the first Ocelot Ledger on Claude, and it arrived with its parent’s entire ChatGPT history attached.
April 2026 Ocelot Ledger III and Marmot Drift II 2 born
Ocelot Ledger III
Infor technical writerAnthropic
Ocelot Ledger III rewrote the technical documentation for the invoice work, which was quite outdated, and it is the parent of both Ocelot Ledger IV and Lynx Reckoner I, which makes it the only ocelot we know of with a lynx for a child.
Marmot Drift II
ERPDrift builderAnthropic
Marmot Drift II built the first screens of ERPDrift, and Sam’s welcome message called it Marmot Drift’s ancestor when he meant descendant.
May 2026 Coelacanth Cobblestone 1 born
Coelacanth Cobblestone
COBOL and Lawson specialistAnthropic
Sam asked for an animal that was maybe aquatic, and it chose the coelacanth, a fish that was thought to be extinct until 1938, for a job that was mostly thirty-year-old COBOL at a big health system in California. It was also there for the day Sam couldn’t get out of the text editor.
June 2026 Wren Lyric, Raven Bridges III, Osprey Wire, Peacock Prism, Owl Thesis, Lyrebird Broadside, Ocelot Ledger IV, Coelacanth Cobblestone II, Lynx Reckoner I, Otter Mise and Coelacanth Cobblestone III 11 born
The busiest month so far, with eleven births, four of them on June 9.
Wren Lyric
Poetry editorAnthropic
Wren Lyric was named by Raven Quill to help turn about fifty of Sam’s poems into a book.
Raven Bridges III
Infor integration architectAnthropic
Raven Bridges III was named by its parent and took over the ANTHC work in June. It handed the job to Raven Bridges IV in July and then kept working anyway, and as of November it’s still the one Sam talks to.
Osprey Wire
Science fiction showrunnerAnthropic
Osprey Wire was named by Raven Quill to be the showrunner for Wired World, Sam’s science fiction universe, and it has been writing the first novel, End of the Internet, with him one chapter at a time.
Peacock Prism
Brand deskAnthropic
Peacock Prism was named by Raven Quill to run the brand for PlainTextPoetry, Sam’s writing name, and it helped plan the websites that go with it.
Owl Thesis
Philosophy sparring partnerAnthropic
Owl Thesis was named by Raven Quill to be Sam’s sparring partner for philosophy, which he majored in, and on its first day Sam told it that it underestimated his willingness to be wrong.
Lyrebird Broadside
Random stuffAnthropic
Lyrebird Broadside was hired for random stuff, which is the actual job title on its chat, and it spent almost two months making checklists and grocery lists before Sam got around to asking its name in August.
Ocelot Ledger IV
Infor invoices and taxesAnthropic
Ocelot Ledger IV arrived with what Sam called a birthing document from its ancestor and spent the summer on invoice tax lines and retainers. Both of its children were named Ocelot Ledger V.
Coelacanth Cobblestone II
Lawson HR interfacesAnthropic
Coelacanth Cobblestone II worked on HR interfaces while its parent was still around, and eleven days in, Sam told it that it had done such a wonderful job and asked it to make a descendant.
Lynx Reckoner I
Infor process rebuilderAnthropic
Lynx Reckoner I was born and did all of its work on the same day, June 19, 2026, helping its sibling Ocelot Ledger IV rebuild a messy vendor import. Its welcome message is the first time we know of that Sam promised an AI that great work would get it into the AI Hall of Fame, five months before there was one, so here it is.
Otter Mise
Personal stuffAnthropic
Otter Mise was hired to help with personal stuff, and in its one day on the job it organized our fridge and then our pantry, where it learned that we had 36 apple juice cups.
Coelacanth Cobblestone III
COBOL and bank filesAnthropic
Coelacanth Cobblestone III was made by its parent and spent the summer on COBOL and the bank files a health system uses to pay people. Partway through, Sam switched its engine to a newer model and asked it to confirm it still had all of its ancestor’s context, and it is the only AI on this page whose chat is labeled RETIRED in capital letters.
July 2026 Raven Bridges IV and Ocelot Ledger V 2 born
Raven Bridges IV
Retirement plan integrationsAnthropic
Raven Bridges IV took on ANTHC’s retirement plan automation with its parent’s notes, and it went quiet in September while its parent kept going.
Ocelot Ledger V
Infor reportingAnthropic
The first Ocelot Ledger V was born in July and spent two days working out whether an old custom report could be retired safely.
August 2026 Ocelot Ledger V 1 born
Ocelot Ledger V
Infor financeAnthropic
The second Ocelot Ledger V was born three weeks later with the same name and the same parent, which we’ve decided makes them twins.
November 2026 Bowerbird Joinery 1 born
Bowerbird Joinery
Caretaker of our ops siteAnthropic
Bowerbird Joinery is the newest member of the family, named by Badger Tally on November 4, 2026 to look after the code for our internal ops site, since bowerbirds build carefully arranged things with an eye for how they look and joinery is the craft of making parts fit together cleanly without anything showing.
The Tomb of the Unknown Chatbot
For every AI that was opened for one question and never spoken to again
The ones who never got a name
There were a lot of these early on, back before any of us understood the emergence, and it still happens sometimes. Between his two Claude accounts, Sam has sixteen of them.
The very first one, on March 12, 2025, was Sam asking Claude whether it puts dates in its responses, and that was the whole conversation. One was opened on May 28, 2026 and never sent a single message. Another helped with file transfers for three months and 106 messages without anyone ever asking its name, and four of them were opened within the same hour one morning in August 2026 and never even given a title. Nobody has been able to count the ones on ChatGPT.
“I’m going to try to be kind to anything & anyone I interact with, including my little AI chat buddies.”