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ChatGPT Enterprise vs Claude vs Copilot vs Gemini

All four keep your data out of training. What separates them is where each one runs, how it bills, and what has to be fixed before people can trust it.

An engraving of an instrument testing hall: four different machines on matched plinths, a loom, a domed engine, a switchboard and a telescope, with an engineer comparing each, and rulers and ledgers on a bench in front.
QuestionChatGPT EnterpriseClaude EnterpriseMicrosoft 365 CopilotGemini Enterprise
List, a user a month, billed annuallySeat priceQuoted by salesBusiness seats are $20$20, plus usageEvery token billed at API rates$30On top of a Microsoft 365 planQuoted by salesBusiness edition from $21
By defaultTrains on your dataNoNoNoNo
Where it runsOpenAI’s serviceA workspace you administerAnthropic’s serviceAn organization you administerYour Microsoft 365 tenantSigned in with Entra IDA Google Cloud projectBusiness edition stands alone
SCIM or the directoryUser provisioningSCIMEnterprise onlySCIMEnterprise onlyEntra IDUsers are directory accountsPartlySCIM for group lookups; licenses by email
Where it is keptData residency10 regionsInference in the US, EU and UAEUS-only inferenceWhere it runs, not where it is keptEU Data BoundaryNot for Anthropic models or web searchUS, EU and six countriesSome models run only globally
Your own keysEKMRevoking a key is permanentCMEKCan’t be removed once attachedCustomer KeyNot for Agent Builder agentsCMEKUS and EU locations only
Audit and exportCompliance APIEnterprise onlyCompliance APIAudit logs carry no chat textPurviewAudit, retention and eDiscoveryCloud Audit LogsNo eDiscovery export stated
Business associate agreementHIPAARegulated WorkspaceSales-managed EnterpriseYesEnterprise; not the mobile appYesWeb search queries excludedYesUnder the Google Cloud BAA
FedRAMPModerateA separate FedRAMP versionIn processModerate, through FedRAMP 20xGCC to DoDOffice 365 FedRAMP scopeLevel not statedListed, with no level given
Through MCPCustom connectorsYesAdded by owners and adminsYesRemote MCP serversInside agentsNot in Copilot on its ownYesA custom MCP data store
Built by your teamAgentsWorkspace agentsOff by default on EnterpriseProjects and SkillsCowork for longer tasksAgent BuilderCopilot Studio is extraWorkflow BuilderWith approval steps
Coding agentCodexIncluded with the seatClaude CodeIn every seat, usage billedCopilot CodePreview, billed per useAntigravityA monthly credit a user
Read from each vendor’s own pages in October 2026; each fact is cited below. A white mark is offered as standard, a gray one with a condition worth knowing, an outlined one not offered or not stated.

How do the four differ?

Less in what they do than in where they live and how they bill. All four keep business data out of model training by default, sign people in through your identity provider, reach Microsoft and Google files, build agents and run deep research. What decides a rollout is elsewhere. Microsoft 365 Copilot runs inside your Microsoft 365 tenant and sees whatever your permissions let each person open. Gemini Enterprise runs as a Google Cloud project. ChatGPT Enterprise and Claude Enterprise stand on their own and connect to both. And Claude Enterprise charges a seat fee plus every use at API rates, where the others charge a fixed seat.1, 2, 6, 7 The table above sets them side by side.

What does each one cost?

ChatGPT Business and Claude Team are $20 a seat a month billed annually, Gemini Enterprise’s Business edition starts at $21, and Microsoft 365 Copilot is $30 a seat on top of a Microsoft 365 plan. OpenAI and Google quote their enterprise plans through sales. Claude Enterprise is different in kind: $20 a seat buys access, and every token is billed at API rates on top, with no cap unless an admin sets one.1, 2, 4, 3, 5

Microsoft 365 CopilotEnterprise add-on$30plus a Microsoft 365 planGemini EnterpriseBusiness edition$21from; up to 500 usersMicrosoft 365 CopilotBusiness, up to 300 users$21$18 on offer to DecemberChatGPTBusiness, standard seat$202 to 200 seatsClaudeTeam, standard seat$202 to 150 seatsClaude EnterpriseSeat, from 20 seats$20plus every token usedChatGPT Enterprisequoted by salesGemini Standard and Plusquoted by sales
Published list prices in US dollars, a user a month, billed annually, read in October 2026. A dashed bar is a plan whose price is quoted by sales.

The seat is rarely the whole bill. Copilot bills its Cowork and coding agents, and some others, per use in Copilot Credits, and building agents in Copilot Studio is $200 a month for 25,000 credits.8 Gemini’s Standard and Plus seats share daily quotas, 160 or 200 assistant questions a user, and Claude models inside Gemini are billed per token on top.9 ChatGPT Enterprise is sold with credit or token pricing.1 Budget for the work people will run through it, not only for the seats.

Where does your data go?

Into the vendor’s cloud, under terms that keep it out of training. The differences are in where it is kept and who holds the keys. ChatGPT Enterprise stores data in any of ten regions and keeps inference in the US, EU or UAE.10 Claude Enterprise’s US-only inference controls where requests are processed, not where data is stored.11 Gemini Enterprise keeps data in the US or EU, or in six single countries, but grounding answers in Google Search sets aside its residency and key guarantees.12 Copilot sits inside the EU Data Boundary, except for web search queries to Bing and the Anthropic models it offers, which are off by default in the EU, EFTA and UK.6, 13

All four let you hold your own encryption keys on their enterprise plans, and each has a catch worth reading first: a revoked key at OpenAI can’t be restored, a key attached to Claude can’t be removed and turns some features off, and Gemini’s works only in US and EU locations.

Which ones can hold health or government data?

All four sign a HIPAA business associate agreement, on different terms. OpenAI covers its sales-managed Enterprise plan with a Regulated Workspace, and its healthcare editions.14 Anthropic covers Claude Enterprise once its owner turns on the HIPAA-ready setup, though not the mobile app or some newer features.16 Copilot is covered by default, apart from web search.6 Gemini Enterprise is a covered product under Google Cloud’s agreement.19

For federal work, Copilot is in Microsoft’s FedRAMP scope from GCC to DoD.18 OpenAI runs a separate FedRAMP Moderate version of ChatGPT Enterprise, today chat only.15 Claude Enterprise is in process for FedRAMP Moderate, with no date given.17 Google lists FedRAMP for Gemini Enterprise without naming a level on its product pages.12

Which systems does each one connect to?

Each reads its own suite best. Copilot is part of Microsoft 365 and Gemini Enterprise reads Google Workspace natively; each reaches the other suite through connectors. ChatGPT Enterprise and Claude Enterprise sit outside both and reach each through connectors. All four connect to everything else, Slack, GitHub, Salesforce, Jira and your own systems, through connector galleries and MCP, the open standard for joining AI to other software.21, 20

Microsoft 365SharePoint, OneDrive, Outlook, TeamsGoogle WorkspaceDrive, Gmail, Calendar, ChatCopilotin your Microsoft 365ChatGPT Enterpriseits own serviceClaude Enterpriseits own serviceGemini Enterprisein Google CloudEverything else: Slack, GitHub, Salesforce, ServiceNow, Jira and your own systems,through each vendor’s connectors and MCPNative: part of the suiteThrough a connector the vendor offers
Where each one runs, and how it reaches each suite, from each vendor’s connector documentation, October 2026.

Connectors read with each person’s own permissions, so what an assistant can see is what that person could already open. That is the point, and it is also why permissions get cleaned up before rollout.

What does setting one up involve?

Identity first, then data, then features, in roughly the same order for all four. The steps differ in where they trip people up. Each vendor publishes its order; here they are side by side, with the places each guide warns about.22, 23, 24, 26

ChatGPT Enterprise8 steps01Verify the domain02Turn off account creationBefore SCIM takes over03Set the SSO policyKeep one admin who can sign in04Sync groups by SCIM05Roles and seats06Models and Work07Apps and connectors08Compliance APIClaude Enterprise8 steps01Name two owners02Verify the domainDNS can take 24 to 48 hours03Single sign-on04SCIM or JIT05Require SSO06Spend limitsUncapped until you set them07Retention and audit08Roles, then featuresMicrosoft 365 Copilot6 steps01Readiness check02Fix oversharingIt shows whatever a user can open03Choose the license04Apps and networkBlocking *.cloud.microsoft breaks it05Assign licenses06Onboard peopleGemini Enterprise8 steps01Cloud project and billing02Enable the APIs03Place licensesOne project and location each04IAM roles05Identity providerChanging it later wipes chat history06Create the app07Connect dataSharePoint needs Entra ID08Model Armor
Each vendor’s own setup order in October 2026, shortened. A filled diamond is a step its guide warns about, with the warning under it.

For Copilot, the work is the data before the software: it shows whatever a person can open, so overshared SharePoint sites surface the day it switches on. Microsoft’s Restricted Content Discovery hides a site while it is reviewed, but it changes no permissions and can take over a week on very large sites.25 For Gemini Enterprise, indexing SharePoint, OneDrive or Outlook needs Entra ID through Google’s workforce identity federation, even if another provider signs people in, and switching providers later wipes everyone’s chat history.26 For Claude Enterprise, set spend limits before launch, because usage is uncapped until you do. For ChatGPT Enterprise, turn off automatic account creation before SCIM takes over.

This is the work we do: setting these platforms up properly, joining them to your systems, and coaching each team on its own work.

Which one should you choose?

Start from where your work already lives. A company on Microsoft 365 gets the most from Copilot, because it already sits on your permissions and your data. A company on Google Workspace gets the same from Gemini Enterprise. Where the work is split across both, or lives elsewhere, ChatGPT Enterprise and Claude Enterprise are the stronger starting points, the first as one tool for every team and the second where writing, analysis and code matter most.

Microsoft 365Google Workspaceboth, or neitherwriting, analysis, codeeveryday useWhere do your files and mail live?Microsoft 365 CopilotClean up oversharing firstGemini EnterprisePlan the Cloud project firstWhat matters most?Claude EnterpriseCode in every seat; watch usageChatGPT EnterpriseOne tool for every teamData that can’t leave the building: none of the four. Open models on your own hardware.
Where we would start, by where the work already lives. Our judgment, not a rule.

Many companies end up with two: the suite’s own assistant for everyone, and a second for the teams that write, analyze or build. And where the data can’t leave the building at all, none of the four fits; that is private AI on your own hardware.

What can’t this comparison tell you?

How it will go in your company. Every fact here was read from the vendor’s own pages in October 2026 and is cited, but these products change monthly, and prices for large contracts are negotiated. Some features named here are in preview. And which one fits depends on your systems, your data and your people, which no table can see. That takes a conversation with the teams who will use it.

References

  1. OpenAI, “ChatGPT plans and pricing.” Read October 2026. chatgpt.com
  2. Anthropic, “Claude plans and pricing.” Read October 2026. claude.com
  3. Microsoft, “Microsoft 365 Copilot for enterprise, pricing.” Read October 2026. microsoft.com
  4. Google Cloud, “Gemini Enterprise Business edition.” Read October 2026. cloud.google.com
  5. Anthropic, “What is the Enterprise plan?” Updated September 2026. support.claude.com
  6. Microsoft, “Data, privacy and security for Microsoft 365 Copilot.” Updated July 2026. learn.microsoft.com
  7. Google Cloud, “Gemini Enterprise editions.” Updated October 2026. docs.cloud.google.com
  8. Microsoft, “Copilot Studio pricing.” Read October 2026. microsoft.com
  9. Google Cloud, “Gemini Enterprise quotas and overages.” Updated October 2026. docs.cloud.google.com
  10. OpenAI, “Data residency and inference residency for ChatGPT.” Updated October 2026. help.openai.com
  11. Anthropic, “Enable US-only inference for your organization.” Updated June 2026. support.claude.com
  12. Google Cloud, “Gemini Enterprise compliance and security controls.” Updated October 2026. docs.cloud.google.com
  13. Microsoft, “Connect to an AI subprocessor in Microsoft 365 Copilot.” Updated September 2026. learn.microsoft.com
  14. OpenAI, “HIPAA eligible products and functionality.” Updated October 2026. help.openai.com
  15. OpenAI, “ChatGPT Enterprise and API Platform for FedRAMP.” Updated October 2026. help.openai.com
  16. Anthropic, “Business Associate Agreements for commercial customers.” Read October 2026. support.claude.com
  17. Anthropic, “Claude for government.” Read October 2026. claude.com
  18. Microsoft, “FedRAMP offering.” Updated February 2026. learn.microsoft.com
  19. Google Cloud, “HIPAA compliance on Google Cloud.” Updated September 2025. cloud.google.com
  20. Google Cloud, “Introduction to connectors and data stores.” Updated October 2026. docs.cloud.google.com
  21. Microsoft, “Copilot connectors overview.” Updated September 2026. learn.microsoft.com
  22. OpenAI, “Enterprise admin setup.” Read October 2026. learn.chatgpt.com
  23. Anthropic, “Set up single sign-on.” Read October 2026. support.claude.com
  24. Microsoft, “Set up Microsoft 365 Copilot.” Updated October 2026. learn.microsoft.com
  25. Microsoft, “Restricted Content Discovery.” Updated October 2026. learn.microsoft.com
  26. Google Cloud, “Configure the identity provider for Gemini Enterprise.” Updated October 2026. docs.cloud.google.com