ConnectWise Email Security vs Upfort: Side-by-Side Comparison (2026)

ConnectWise Email Security

Mid-market and SMB security teams drowning in phishing and BEC attacks will see immediate ROI from ConnectWise Email Security, specifically because its identity analysis engine catches impersonation attempts that signature-based filters routinely miss. The platform scores high on NIST DE.CM and DE.AE, meaning it's built to detect anomalies and characterize incidents rather than just block known threats. Skip this if you need advanced DLP with granular content fingerprinting or if your organization runs email on-premises; ConnectWise assumes cloud-first deployments and treats DLP as secondary to threat detection.

Upfort

SMBs and startups drowning in point tools should pick Upfort for its actual integration of security detection with cyber insurance underwriting, cutting your admin overhead in half. The platform covers nine NIST CSF 2.0 functions including continuous monitoring, incident response, and awareness training, deployed in weeks rather than months through modular architecture. Skip this if you need deep endpoint forensics or have complex multi-entity compliance requirements; Upfort trades investigative depth for speed and insurance-backed risk transfer, which works only if underwriting automation actually matters to your board.