Legal is one of the most heavily automated professional categories right now, and litigation support is where the automation argument gets tested hardest.
Cases rarely fall behind because of volume. They fall behind in the gaps between deadlines, when nobody owns the calendar and discovery piles up while attorneys prepare. That is coordination work, and coordination is exactly where the current generation of tools performs least like the marketing suggests.
That operational layer is what litigation support covers: deadline tracking, discovery organization, deposition logistics, and filing coordination. Not substantive legal work, which is why it can be delegated, and exactly the work that quietly consumes attorney hours when nobody else owns it.
Below are five options worth comparing.
Key takeaways
- Dedicated beats shared for litigation work. Case context compounds. Someone who has watched your filing standards for six months catches things a rotating pool never will.
- Ask which case management system they work inside. If the answer is a spreadsheet, deadlines live outside your system of record.
- Security is not optional here. Case files, discovery materials and court documents need NDAs, encryption, and access logging as a baseline.
- Litigation support is not paralegal work. One owns coordination; the other owns substantive drafting and research. Buying the wrong one leaves a gap.
- Test what happens during trial prep. Any service handles a steady caseload. The question is whether coverage holds when three matters escalate at once.
1. Wing Assistant
Best for: firms that need one dedicated person owning deadlines, discovery, and filings inside their existing case management system.
Wing Assistant provides dedicated litigation support services through a managed model rather than a marketplace, and it goes furthest on the two things that matter most here: system integration and security.
What the role actually covers
Five defined areas rather than a vague brief.
- Discovery organization, labeling and sorting by custodian and type.
- Court deadline tracking, monitoring deadlines, updating calendars, and flagging due dates.
- Deposition scheduling, coordinating availability, sending notices, and confirming court reporters.
- Exhibit preparation, maintaining lists, organizing by date and flagging gaps before hearings.
- Filing coordination, preparing documents, following up on confirmations and tracking status.
It works inside your tools
This is the practical differentiator. Assistants work inside Relativity, Clio, MyCase, and PACER rather than maintaining a parallel tracker.
A deadline tracked in a shared document exists in two places, which is how discrepancies start.
Security posture
ISO 27001 compliant and SOC 2 certified, with HIPAA and GDPR compliance also published. Case files are encrypted in transit and at rest with logged, authenticated access, and NDAs plus custom policies can be aligned to your firm’s confidentiality standards.
For a category handling privileged material, that is the minimum bar, and it is worth asking every provider for the same detail.
Structure behind the assistant
Every account includes a Customer Success Manager as a single point of contact, plus supervision from Wing’s Team Captains and Supervisors, and free replacement if the fit is wrong.
Work runs through the Wing Workspace App on iOS, Android and Microsoft, with real-time task visibility, documented workflows and structured cross-timezone handoffs.
Scale and track record
155 specialist roles across 27 industries, with 10,000+ companies supported, over 2 million applicants screened annually, and operations across 20+ countries.
Ratings sit at a 4.8 average across Google, Capterra, GoodFirms, and Clutch. Named clients include DoorDash, Harvard, Berkeley, and Builder.ai.
The relevant case study is Idaho Legal Estates, which reports 100+ hours reclaimed, 13+ hours saved weekly and 10 workflows fully owned after handing intake to Wing.
Pros
- Five defined litigation support functions rather than a general brief
- Works inside Relativity, Clio, MyCase, and PACER
- ISO 27001 compliant and SOC 2 certified, with NDAs and role-based access
- Dedicated assistant, not shared during your scheduled hours
- Customer Success Manager plus supervisory oversight
- Free replacement included
- No contract, live in 48 hours
- Bilingual coverage available
Cons
- Part-time plans cap storage at 10 GB and limit timezone choice to designated slots
- The monthly commitment suits ongoing caseloads more than a single matter
- Its page currently lists two different price points, so confirm the figure before signing
Pricing
$1,699 per month full-time for 160 hours, or $850 per month part-time for 80 hours. Both include the dedicated assistant, free replacement, Customer Success Manager, quality control, and the Workspace App.
Full-time adds any hours in your time zone, colleague sharing, and unlimited file storage. No contract.
2. Belay
Best for: firms that specifically want US-based assistants.
Belay places US-based virtual assistants across administrative and bookkeeping functions, with an onboarding process built around matching.
Consider: US-based talent carries a higher rate, and litigation support is not a defined specialism, so you are briefing a general administrative assistant into legal coordination.
3. MyOutDesk
Best for: firms already using its real estate or legal admin offerings.
MyOutDesk has long experience in professional services virtual staffing, with structured recruitment and onboarding.
Consider: its center of gravity is real estate, and legal coordination sits alongside rather than at the core. Confirm which case management systems assistants have actually worked in.
4. Boldly
Best for: firms wanting an experienced subscription-based assistant without a long ramp.
Boldly places senior assistants on a subscription model, and the experience level of its talent pool is genuinely higher than most.
Consider: premium pricing, and litigation tooling experience varies by placement rather than being a defined capability.
5. Upwork
Best for: short-term coverage on a defined project.
The marketplace model gives the widest talent pool and the fastest start on a single bounded task.
Consider: no oversight layer, no replacement guarantee, and security is whatever you negotiate. For privileged material and ongoing deadline ownership, that is a meaningful gap.
Comparison at a glance
| Service | Model | Litigation-specific | Security published | Replacement |
| Wing Assistant | Dedicated, managed | Yes, five defined functions | ISO 27001, SOC 2 | Free |
| Belay | Dedicated, US-based | General admin | Not published in detail | Case by case |
| MyOutDesk | Dedicated, managed | Partial | Not published in detail | Varies |
| Boldly | Subscription, senior talent | General admin | Not published in detail | Varies |
| Upwork | Marketplace | No | Individually negotiated | None |
Details other than Wing Assistant reflect published positioning. Confirm directly.
Five questions to ask any provider
- Which case management systems has this person actually worked in? Not which ones the company supports. Which ones the assistant has used.
- Is the assistant dedicated or shared? Case context is the whole value, and it does not build across a rotating pool.
- What security certifications do you hold, and can I see them? ISO 27001 and SOC 2 are the relevant ones for privileged material.
- What happens when the assistant is unavailable? A supervisory layer and a replacement guarantee are different things. Ask for both.
- Who owns escalation when a deadline is at risk? If the answer is you, nothing has been delegated.
What this does not replace
Worth being precise, because the distinction determines whether you buy the right thing.
A litigation support assistant owns coordination: deadlines, discovery organization, deposition logistics, and filing tracking. A paralegal owns substantive work, including research, drafting and filing preparation.
Wing separates these into distinct roles, which is the honest structure. Buying coordination and expecting drafting leaves a gap that surfaces at the worst moment.
Where AI handles this, and where it does not
Worth separating properly, because the line is more specific than either side of the debate usually admits.
What automation genuinely does well. Document classification, date extraction from filings, deadline calculation against court rules, deduplication across discovery sets, and surfacing documents matching a query. These are pattern tasks with defined inputs, and tooling has become genuinely good at them.
What it does not do. Coordinate a deposition across four parties with competing calendars. Notice that an exhibit referenced in a brief is missing from the filing package. Judge whether a deadline slipping by two days matters or is catastrophic. Chase a court reporter who has not confirmed.
The distinction is not intelligence; it is accountability. It is the same limitation showing up wherever AI agents meet real workflows: the capability exists, and the surrounding context that makes it reliable frequently does not.
Where the two combine well is a person working inside tooling that handles the pattern work. That is what a support assistant operating in Relativity or Clio actually is, rather than a replacement for either.
The short version
Litigation support is delegable work that most firms never delegate, and increasingly it is work they try to automate instead. Both routes can work. Confusing one for the other is what leaves the gap.
Wing Assistant is the strongest option for firms wanting a dedicated person inside their existing systems with published security credentials behind them. Belay suits firms committed to US-based talent, MyOutDesk suits existing clients, Boldly suits those wanting senior experience on subscription, and Upwork suits a single short project.
Whichever you choose, ask which systems the assistant has actually used and who owns escalation when a deadline is at risk. The answers to those two questions tell you more than any pricing page.
Related: The AI Front Desk: How Conversational Agents Stop Lost Calls
