IT support for Clio, MyCase and other legal software

Who can support Clio or MyCase for a law firm in Dallas?

I can. I am Anthony Omini, owner of Cross River Tech, a small managed IT company in Dallas that works with law firms among a handful of other industries, and I am the person you deal with directly. I support Clio, MyCase, PracticePanther, Smokeball, CosmoLex and the other cloud practice management platforms that small and mid-sized firms run on, along with the Microsoft 365, document storage and e-signature tools they plug into. I say "support" on purpose; the vendors run those programs, and the honest description of my role is that I make sure everything around them works and is secure, and I get on the phone with the vendor when the problem is on their side.

Here is the short version of how it works. Clio and MyCase live in a browser and in phone apps. When a firm calls me because "Clio is not working," the cause is almost never Clio. It is a Microsoft 365 account that has been locked, an Outlook add-in that stopped signing in after a Windows update, a laptop whose OneDrive is out of sync, a browser extension blocking a page, a document that will not open because the person's permissions changed, or a Wi-Fi network that drops every time someone starts the microwave. Those are IT problems, and they are what I fix, usually remotely and often the same day.

The full picture of how I work with firms is on the IT support for law firms in Dallas page. This article goes deeper on the software specifically: what supporting it means, how it connects to Microsoft 365, where documents should live, how e-signature fits, and how to keep all of it secure.

What does supporting cloud legal software actually mean?

Cloud practice management software divides the work between the vendor and your IT. Confusion about who owns what is why firms sometimes bounce between the vendor's support desk and their IT company while the problem stays unfixed. Here is how I draw the line.

The practical benefit of having me as your contact for the right-hand column is that you never explain your setup twice. I know which attorneys use the Outlook add-in and which prefer the web, which paralegal has the scanner that misbehaves, and where the firm's templates live. That knowledge is what makes a five-minute fix take five minutes.

How do Clio and MyCase connect to Microsoft 365?

Nearly every small firm I work with runs Microsoft 365 for email, calendar and Office, and the practice management software sits on top of it. The connections are useful and they are also where most of the day-to-day problems come from, so it is worth knowing what they are.

• Sign-in. Clio and MyCase can use your Microsoft 365 account as the login, which means one password, one MFA, and one place to close access when someone leaves. I recommend turning this on where the plan allows it.
• Email and calendar. The Outlook add-in files emails to matters, syncs calendar events and deadlines, and shows matter details next to the message. It is the feature attorneys use most and the one that breaks most, usually after an Office update, a password change or a permissions change in 365. I deploy the add-in centrally so it appears for everyone rather than being installed one desk at a time.
• Contacts. Client and contact syncing between the practice software and Outlook, which can produce duplicates if it was set up twice by two different people.
• Documents. Word and Excel documents created from templates in Clio or MyCase, opened in Office, and saved back. When the sync between Office, OneDrive and the practice software's storage misfires, people end up with three versions of a brief.
• Teams. Some firms link matter communication to Teams channels; I make sure that is deliberate and that external sharing is controlled.

The things that keep these integrations healthy are on the Microsoft 365 side: consistent accounts, MFA that does not surprise the add-in, permissions granted by an administrator once rather than by each user, and Office kept on a current version. I cover the security half of that in Microsoft 365 security for a small business, and the same settings protect the practice software because they share a login.

Where should a law firm's documents live?

This is the decision that matters most and the one firms most often make by accident. Client documents end up partly in the practice software, partly in OneDrive, partly on a server from the old office and partly on someone's laptop. When an associate leaves or a laptop is stolen, nobody knows what was where. Decide on purpose.

The choices I see working for small and mid-sized firms in Dallas:

• The practice software's own storage (Clio Drive, MyCase documents). Simple, tied to the matter, searchable from the software. Fine for many small firms. The questions to ask are how the storage syncs to desktops, how much is included, and how you get everything out if you ever leave.
• SharePoint and OneDrive in Microsoft 365, with a folder structure by client and matter and the practice software linking to it. Good when the firm already lives in Office, wants Word to just work, and wants to control permissions from one place. This is the option I set up most.
• A dedicated document management system such as NetDocuments or iManage. More structure, versioning, ethical walls and matter-centric security. Worth it for litigation practices, firms with many matters and many hands, or firms whose clients ask about document controls. Costs more and needs a real rollout.
• An on-premises file server. Still right for some firms, particularly those with very large scanned records or applications that need it. It needs power, backup and someone watching it, which is where managed IT services earn their keep.

Whichever you choose, two rules. First, the practice software is not the backup. If a document lives only inside Clio or MyCase, make sure a copy is backed up somewhere the firm controls, and the same applies to SharePoint. Second, nothing client-related lives only on a laptop. Laptops sync to the firm's storage, or they are not used for client work. The longer version, including e-discovery, is in document management, backup and e-discovery infrastructure for law firms.

How does e-signature fit in?

Engagement letters, settlement agreements, verifications and client intake all go out for signature, and most firms use either the e-signature built into the practice software or a stand-alone service like DocuSign or Adobe Acrobat Sign. I support both. The IT side of e-signature is smaller than people expect and it comes down to four things.

• Accounts. The e-signature service is another door into client documents. It gets MFA, it gets a real firm email address rather than a personal one, and it is included in the offboarding list when someone leaves. I have seen departed staff still able to send documents under a firm's name because the DocuSign login was never closed.
• Where signed documents land. A signed agreement should flow back into the matter, not sit in an inbox. I set up the integration so completed documents file to the matter in Clio or MyCase, or to the right SharePoint folder, automatically.
• Templates and fields. Engagement letter templates with signature fields already placed save real time, and someone has to build and maintain them. That is usually a short project.
• Phishing that imitates e-signature. Fake "you have a document to sign" emails are one of the most common phishing lures aimed at law firms, precisely because firms sign things all day. External email tagging, Safe Links and a short reminder to staff to open the signing service directly rather than from a link cut the risk considerably.

Whether a particular e-signature meets the requirements of a given court or transaction is a legal question for you, not an IT one for me. What I make sure of is that the service is set up securely, that signed documents are stored and backed up with the matter, and that nobody outside the firm can use your account.

How do you keep legal software secure?

The practice software holds everything a client told you. Keeping it private is a professional duty and, in practical terms, a set of settings and habits. Here is what I put in place, in order of importance.

1. MFA on the practice software itself, as well as on Microsoft 365. If sign-in uses the Microsoft account, one MFA covers both; if not, both need it. An attorney's Clio password in a data leak should not open the firm's matters.
2. Roles and permissions that match the firm. Not every user needs to see every matter, export the client list, or change billing. I set roles with the managing attorney and review them when staff change.
3. Encrypted devices. Every laptop and phone that touches client data has full-disk encryption on and a screen lock that actually engages. A lost laptop then is a lost laptop, not a notification to clients.
4. Controlled sharing. Client portals and secure links instead of email attachments for anything sensitive, and external sharing in SharePoint limited to what the firm decides.
5. Same-day offboarding across every system. Microsoft 365, the practice software, document storage, e-signature, the phone system, the VPN and the door code. I keep a checklist per firm so nothing is missed at 5 PM on someone's last day.
6. Audit trails turned on. The practice software and Microsoft 365 both record who accessed what. Nobody reads the logs daily, but when a question comes up, the answer exists.
7. Backups the firm controls. Practice software exports and Microsoft 365 backups, tested by actually restoring something.

None of this requires expensive products. It requires someone who knows the firm's setup and does the unglamorous parts consistently. The wider picture, including secure email, phishing aimed at settlement funds and what "helps you meet" confidentiality duties means in practice, is in law firm cybersecurity and client confidentiality.

What does a typical support call from a law firm look like?

Concrete examples say more than a list of services, so here are the kinds of calls I take from firms, with what the fix usually turns out to be. Details are generic; I do not name clients.

• "The Clio add-in disappeared from Outlook after the update." The add-in needs to be re-deployed from the Microsoft 365 admin center, or Outlook's cached credentials need clearing. Remote, usually under an hour.
• "MyCase says my session expired every few minutes." A browser extension or a conditional access rule requiring frequent re-authentication for a device that is not marked compliant. Remote fix on the device or the rule.
• "A paralegal can see a matter she should not." A permission group in the practice software that was set up years ago and never reviewed. Fixed with the managing attorney on the call.
• "Documents from the template open as read-only." OneDrive sync conflict or a file locked by a previous session. Remote.
• "We hired an associate starting Monday." Microsoft 365 account, practice software license, e-signature seat, phone extension, laptop set up with encryption and the add-ins, access to the right matters. Mostly remote, one onsite visit if the laptop needs delivering.
• "The scanner stopped sending to the matter folder." Scan-to-folder credentials expired after a password change. Remote, sometimes onsite for older scanners.
• "We got an email from a client changing their wiring instructions." Stop. Do not act on it. Call the client on the number you already have. Then I look at whether either mailbox has been compromised.

Remote support is available 24/7/365 with after-hours rates, onsite visits are by appointment across Dallas–Fort Worth, and for firms on a managed plan remote support is unlimited and included. A solo attorney or a two-person office sometimes prefers hourly, and I cover that in IT support for solo attorneys and small law offices.

What about desktop legal software and servers?

Not every firm is in the cloud. Plenty of established Dallas practices still run PCLaw, Time Matters, Tabs3, Worldox or an older document management system on a server in a closet, with attorneys connecting over remote desktop from home. I support those too, and I am not going to tell you to migrate just because it is fashionable.

What a server-based firm needs from me is different: keeping the server patched and backed up with a tested restore, keeping remote desktop access behind MFA and a VPN rather than open to the internet, making sure the software vendor's updates are applied on a schedule that does not land in the middle of a filing deadline, and planning the hardware's replacement before it fails rather than after. Those are exactly the things included in a managed plan.

When a firm does decide to move to Clio, MyCase or another cloud platform, the migration is a project I can run end to end: exporting matters, contacts, time entries and documents from the old system, cleaning them up, importing them, setting up the Microsoft 365 side, running both systems side by side for a short period, training the staff on the parts that change, and decommissioning the server properly afterwards, with its data retained for as long as the firm's retention policy says. The vendors provide import tools and guidance; I provide the person who has done it before and who will still be answering the phone six months later.

How do you get started with me?

The first conversation is short and free. Get in touch or call (214) 612-7080 and tell me which practice software you run, how many attorneys and staff you have, whether you are on Microsoft 365 or Google Workspace, and what is bothering you today. From that I can tell you whether the fix is a one-time hourly job or something a monthly plan would cover, and what I would look at first.

For firms that want ongoing support, managed IT is quoted per user or per device after that conversation, month-to-month with no annual contract, and includes unlimited remote support, onsite when remote cannot fix it, updates, antivirus and email security, backup, and management of the office network. For firms that want a specific project, such as a migration or a security review, I quote the project and bill by the hour.

You deal with me directly, which means I know your firm's setup by heart, you never re-explain it to a new technician, and there is no ticket queue between you and the fix. My team handles the routine monitoring and updates behind me, and I am honest about capacity: onsite work is scheduled by appointment. Firms in Dallas, Plano, Fort Worth and across the metroplex can see their local page under service areas; for firms elsewhere in Texas, almost everything about cloud legal software is supported remotely.

Questions people ask

Written and reviewed by

Anthony Omini, founder of Cross River Tech

Over 15 years in IT across many industries, now running Cross River Tech, a small owner-led managed IT company in Dallas. Every article is written from his own client work and checked by him before it is published.

Tired of bouncing between the vendor and IT? Tell me which practice software your firm runs and what is not working. I will tell you whose problem it is and fix the part that is mine.

Ask Anthony(214) 612-7080About Anthony