Sources

Customization & workflows: Clio (Automated Workflows, Custom Fields), MyCase (Workflows, Custom Fields, Advanced Doc Automation), CARET (Custom fields, Workflows, Doc Automation/HotDocs).
Docs & files: Clio Drive & integrations; MyCase Drive; CARET OneDrive.
Accounting: Clio Accounting; MyCase Accounting; CARET native accounting.
Outlook/Calendar/Email: Clio Outlook add-in & O365 sync; MyCase Outlook add-in & calendar sync; CARET email/Outlook plugin.
Migrations & training: Clio pricing/migration pages; MyCase migration & guided implementation; CARET migration FAQ & pricing.

A note on Outlook changes

Microsoft’s new Outlook for Windows supports web add-ins (like Clio’s and MyCase’s). COM add-ins aren’t supported in new Outlook (they still work in classic Outlook).
CARET’s plugin is a classic desktop plugin and isn’t compatible with new Outlook or OWA as of the latest documentation. Plan accordingly if your IT roadmap includes the new Outlook.

• Custom fields. All three let you add contact/matter fields that also power merge fields in document templates. This is the backbone of “your firm’s way” in the cloud.
• Document automation.
  • Clio: Word-based templates are built into Clio Manage; Clio Draft adds advanced templating, conditional logic, and questionnaire-driven assembly.
  • MyCase: Two paths—web-based templates or a Word add-in for Advanced Document Automation.
  • CARET Legal: Classic Word merge with firm fields; HotDocs integration for complex assemblies (estate planning, high-variable docs).
• Workflows.
  • Clio: Automated Workflows chain tasks, docs, and matter stages.
  • MyCase: Workflow templates push task lists and dated events into cases.
  • CARET Legal: Workflow templates that auto-create events and tasks by practice area.

Practical tip: Before migration, build a one-page “field map” (legacy → new). That avoids the classic “where did we put the docket #?” scavenger hunt.

Clio

Included: For many systems, Clio offers complimentary migration covering core records (contacts, matters, activities/time, calendar events, tasks, notes, custom fields). They provide CSV templates and a guided process. Documents are typically moved via Clio Drive or connected DMS rather than through CSV.

MyCase

Included: Free migration is a selling point. Their onboarding team usually moves data in two phases, starting with contacts, matters/companies, and custom fields, then other items.

CARET Legal

Included/Managed: CARET runs migrations in-house; the standard project is 6–10 weeks depending on scope and brings forward WIP, AR, Chart of Accounts, and vendors in addition to case data. You get a dedicated onboarding PM.

Timing reality check: Documents and email are the long poles. CSVs handle structured data quickly; terabytes of folders and old email take planning and bandwidth. Use your platform’s desktop drive (Clio Drive/MyCase Drive) to drag folders in batches; test performance and naming conventions.

• Clio: 24/5 support and a solid library of free, on-demand courses through Clio Academy for admins and users.
• MyCase: Guided implementation for eligible firms plus live training sessions and a Learning Center.
• CARET Legal: Project-managed onboarding, topical training webinars, and on-demand videos.

Adoption tip: Treat this like a phased rollout: pilot a practice group, measure, then scale. And schedule mandatory “hour of power” sessions where each team member builds one workflow and one doc template—ownership beats sermons.

• EWS retirement hits Exchange Online in October 2026. If your legacy system’s server-side sync leans on EWS, the connection can fail for Microsoft 365 tenants. Plan accordingly; the modern path is Microsoft Graph + web add-ins (what newer cloud tools already use).
• New Outlook vs. classic Outlook. New Outlook for Windows doesn’t support COM add-ins; web add-ins are the future. Desktop COM plug-in workflows (e.g., CARET’s current Windows plugin) won’t work in new Outlook or Outlook on the web—classic Outlook still supports them, but firms are trending toward the new client.

Small firm, wants fast time-to-value, minimal moving parts: MyCase
Why: All-in-one approach, quick migration, native accounting and MyCase Drive keep your stack simple. The Outlook add-in and 2-way calendar are straightforward.

Growing firm that values flexibility, deep automation, and integrations: Clio
Why: Robust app directory, Automated Workflows, advanced document automation with Clio Draft, and the option to keep books in Clio Accounting or stay on QuickBooks/Xero. Broad Microsoft/Google sync and an Outlook add-in that also works on the web.

Mid-size/multi-office firm with complex accounting and HotDocs templates: CARET Legal
Why: Native GL & trust accounting, AP/AR, and managed migrations. Excellent for firms that want time capture inside email and are fine staying on classic Outlook for the plugin—or using CARET’s built-in email client.

• Move within the family to CARET Legal (smoother mapping of concepts; familiar Outlook-centric workflows if you keep classic Outlook).
• Jump to a cloud-native leader (Clio/MyCase) if you want web add-ins, broad integrations, and modern automation.

60–90 days before cutover

• Inventory & archive. List data sources (matters, contacts, time, AR, trust, docs, email). Close/archive dormant matters; dedupe contacts.
• Field map. Create the legacy → new custom field map; list template names and where each merge field lands.
• Pick your path. Choose vendor, tier, and the migration window; identify PM, pilot group, and success metrics (billing cycle time, adoption rate, % emails filed to matters).
• Security & roles. Define permission sets and test MFA/SAML.

30 days before cutover

• Dress rehearsal. Vendor runs a test import with a live data slice. Validate with attorneys and accounting (especially WIP, AR, and trust balances).
• Document move plan. Use Clio Drive/MyCase Drive—or OneDrive/NetDocuments with Clio—to bulk-move folders in batches. Name conventions and client-matter trees get locked now.
• Templates & workflows. Rebuild at least your top 10 templates and 3 workflows per practice area; test end-to-end.

Cutover week

• Blackout window. Freeze changes in the legacy system while migration runs; track anything that happens during blackout on a spreadsheet for manual entry.
• Train by role. Short, role-specific sessions: Intake, Docketing, Billing, Partners.
• Go live. Keep a “war room” chat and daily stand-ups.

Week 2–4

• Bill cycle shakedown. Send first invoices, reconcile bank/trust (Clio Accounting / MyCase Accounting / CARET).
• Retrospective. What took too many clicks? Add or refine workflows; tune document templates.

• Clio: Outlook add-in files email (including attachments) to matters; supports Outlook desktop and Outlook for the web. Office 365 contact & calendar sync is supported.
• MyCase: Outlook add-in for email filing; 2-way Outlook calendar via the MyCase calendar.
• CARET Legal: In-app email client with O365/Gmail (or IMAP), plus a Windows desktop Outlook plugin. As of current docs, the plugin doesn’t work in the new Outlook or OWA. If your IT plans to standardize on new Outlook, weigh that carefully.

Whichever you choose, lock your field map, rehearse the migration, and treat training like a client deadline. Do that, and your “move to the cloud” won’t be a leap—it’ll be a clean, well-documented step.