ConnectWise
Depends
Confidence: Medium
Buy only if you run a mid-size or large MSP with dedicated admins and budget for a quote-based, all-in-one PSA/RMM suite.
New check
Comparison
ConnectWise vs DeskDay
ConnectWise and DeskDay both land on Depends.
DeskDay
Depends
Confidence: Medium
Buy if you run a small MSP (roughly 1-10 techs) that wants chat/Teams-first ticketing at $59 per tech.
| Compare | ConnectWise | DeskDay |
|---|---|---|
| Verdict | Depends | Depends |
| Best for | Mid-size to large MSPs | Small MSPs (1-10 techs) |
| Who it's not for | Small IT shops wanting simple ticketing | Large MSPs needing deep billing/procurement PSA |
| Privacy | Turbulent: 2024-2026 ScreenConnect RCEs and a confirmed nation-state breach; vendor does publish bulletins.⁶ | No known public vulnerabilities found in the sources reviewed. |
| Support quality | Recurring Reddit helpdesk complaints | No evidence in reviewed sources. |
| Public sentiment | Reddit MSP sentiment skews negative . praise for PSA depth, anger at RMM quality, support, and pricing. | Reddit users call it a strong fit for small MSPs but note the product is still maturing, and formal review counts are tiny.15 |
| Biggest gotcha | Pricing is quote-only; expect per-tech fees, negotiation, and reported hidden charges³ | Public review footprint is tiny (3 G2, 1 Trustpilot review) . weak reliability signal. |
Pick ConnectWise when
- Mid-size to large MSPs
- Teams consolidating PSA, RMM, remote access
- MSPs with dedicated platform admins
- High endpoint volumes
When ConnectWise is not a fit
- Small IT shops wanting simple ticketing
- In-house IT without admin bandwidth
- Buyers needing transparent pricing
- Security-sensitive orgs uncomfortable with breach history
Pick DeskDay when
- Small MSPs (1-10 techs)
- Chat-first support teams
- Microsoft Teams-centric IT helpdesks
- Teams outgrowing spreadsheets
When DeskDay is not a fit
- Large MSPs needing deep billing/procurement PSA
- Buyers who need a proven track record
- Non-IT helpdesks (MSP-specific design)
- Teams needing large integration ecosystems
Sources
- ConnectWise official siteconnectwise.comofficial
review
- ConnectWise pricing guide (Superops)superops.comreview
- Companies using ConnectWise (Enlyft)enlyft.comnews
- Thoma Bravo buyout financing (Private Equity Wire)privateequitywire.co.uknews
security
- CVE-2025-14265 ScreenConnect RCE (SentinelOne)sentinelone.comsecurity
- New ScreenConnect flaw without patch (BleepingComputer)bleepingcomputer.comsecurity
review
- ConnectWise security bulletinsconnectwise.comofficial
- DeskDay Pricing and Plansdeskday.comofficial
- Deskday PSA : r/mspreddit.comreview
- Anyone use DeskDay? : r/mspreddit.comreview