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PSA for managed service providers · ConnectWise PSA

AI automation for ConnectWise PSA

ConnectWise PSA, formerly Manage, is the ticketing, billing and agreement system for many managed service providers. Service desks drown in tickets with long email chains, vague subjects and missing context. Dispatchers spend time reading instead of assigning, and account managers find out about unhappy clients at renewal time.

InTheory is independent and not affiliated with ConnectWise PSA. Product names are trademarks of their owners.

ConnectWise Sidekick for PSA adds AI ticket summarization written back as a note, auto-triage and categorization, customer sentiment tracking, translation into more than 10 languages, suggested resolutions and reply drafts, plus a Microsoft Teams chat interface. For anything beyond that, ConnectWise PSA has a well-used REST API, and many MSPs already run integrations through it.

Practical automations

Ticket summaries for dispatch

Generate a short summary note on long tickets so the dispatcher can assign quickly. Track time from ticket creation to assignment.

Auto-triage and categorization

Let Sidekick set board, type and priority on new tickets. Review a sample of AI categorizations weekly and correct the rules.

Sentiment flags for account managers

Surface tickets with negative sentiment to the account manager for a personal call. Do not send automated apologies.

Suggested resolutions from history

Show engineers similar past tickets and fixes. The engineer decides what applies and documents what actually worked.

Client-facing reply drafts

Draft update emails to end users in plain language. The engineer checks technical accuracy before sending.

QBR prep from ticket data

Pull ticket counts, categories and SLA results through the API and draft quarterly business review notes. The vCIO edits the recommendations.

Commonly connected to

ConnectWise AutomateConnectWise RMMMicrosoft TeamsMicrosoft 365IT GlueQuickBooks Online

Pitfalls to avoid

  • Letting AI close or merge tickets without a human check, which hides recurring problems.
  • Suggesting fixes from old tickets that no longer match the client's current environment.
  • Building API integrations without rate limits, logging or an owner, so failures go unnoticed.

When not to automate

If your boards, types and priorities are inconsistent, AI triage will copy the mess; clean the setup first. A small MSP with one dispatcher who knows every client may get little from summaries. Security incidents, access changes and anything affecting client systems stay with a qualified engineer, not an AI suggestion.

Common questions

What is ConnectWise Sidekick for PSA?

Sidekick for PSA is ConnectWise's AI assistant inside the PSA. It summarizes tickets, auto-triages and categorizes them, tracks customer sentiment, translates ticket content, suggests resolutions and drafts replies, and works through Microsoft Teams. Check ConnectWise for current packaging and pricing.

Should we use Sidekick or build our own with the API?

Start with Sidekick for summaries and triage, since it already sees your tickets. Build on the API only for gaps such as custom QBR reporting or links to documentation tools. Custom work needs an owner and monitoring.

What should we measure at the service desk?

Time to assign, time to first response, first-touch resolution rate, reopened tickets and the number of tickets that miss SLA. Compare a month before and after turning on each feature.

Industries that use ConnectWise PSA

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