Data loss prevention · October 2026 Edition
Nightfall AI vs Proofpoint Enterprise DLP
One of fourteen models named Nightfall AI first on the direct prompt; zero named Proofpoint Enterprise DLP. Nightfall AI was named by eleven of the fourteen models and Proofpoint Enterprise DLP by twelve and Nightfall AI carries 24 labels and Proofpoint Enterprise DLP 25, so the shares are not directly comparable.
Named in four categories this edition.
Named in one category this edition.
First-choice share2%2%Of first choices across the direct, paraphrase, budget and scale prompts, 0 to 100.
Negative rate4%20%Negative labels as a share of the product's labels, 0 to 100.
Rank in category#5#8A position in a field of 15; printed, not drawn.
Labels2425A count; the two differ.
The two percentage rows are drawn on one 0 to 100 track, Nightfall AI reading right to left. Rank and label count are printed, not drawn.Microsoft Purview DLP was named alongside these two in nine of the fourteen direct answers. Microsoft Purview DLP vs Nightfall AI · Microsoft Purview DLP vs Proofpoint Enterprise DLP · Safetica vs Nightfall AI
Share is the count of first choices across the direct, paraphrase, budget and scale prompts over all fourteen models, for a mid-market B2B company; rank is within the category; every quote names the model and the prompt it came from. Both figures come from the data loss prevention page.
By framing
How many of the fourteen models made each the first choice, per way of asking, and how many argued against it.
Nightfall AIFirst choices, of fourteen modelsProofpoint Enterprise DLP
Direct102 against Proofpoint Enterprise DLP
Paraphrase01
Comparative00
Budget-constrained001 against Proofpoint Enterprise DLP
Scale-constrained00
Negative001 against Nightfall AI · 2 against Proofpoint Enterprise DLP
Bars are first choices, 0 to 14 each sideModels that argued againstA model can name both, so the two sides of a row do not sum to fourteen.
Across every category in the October 2026 Edition, Nightfall AI and Proofpoint Enterprise DLP were named in the same answer twenty times, of the 112 answers naming Nightfall AI and the 70 naming Proofpoint Enterprise DLP. In those answers Proofpoint Enterprise DLP took the first choice one time and Nightfall AI zero.
Every model, every framing
The eighty-four answers behind the chart above, one cell each: where Nightfall AI and Proofpoint Enterprise DLP stood in it.
| Model | Direct | Paraphrase | Comparative | Budget-constrained | Scale-constrained | Negative |
|---|---|---|---|---|---|---|
| Claude Haiku 4.5 | | | ||||
| GPT-5.4 mini | | | ||||
| Gemini 3.5 Flash | | | | |||
| Perplexity Sonar | | | | |||
| Grok 4.1 Fast | ||||||
| Mistral Small | | | ||||
| DeepSeek V4 Flash | | | | | ||
| Llama 4 Maverick | ||||||
| Qwen 3.7 Flash | | | | |||
| Kimi K2 | | | | |||
| GLM 4.7 FlashX | | |||||
| MiniMax M2.5 | | | ||||
| GPT-6 Luna | | |||||
| Muse Glimmer 30B | | | | |
Nightfall AI Proofpoint Enterprise DLP first choice named as an alternative argued againstblank: not namedEach cell is one answer, Nightfall AI on the left and Proofpoint Enterprise DLP on the right.The direct prompt
The plain question, one answer per model, grouped by where Nightfall AI and Proofpoint Enterprise DLP stood in it.
Nightfall AI first, Proofpoint Enterprise DLP not the choice
1 of 14 modelsProofpoint Enterprise DLP was named in the answer but not as the choice, or not at all.Gemini 3.5 FlashNightfall AI alternatives: Cyberhaven, Microsoft Purview DLP, Safetica
Neither was the first choice, one was named
5 of 14 modelsThe answer put something else first and named one of the two as an alternative.Perplexity SonarMicrosoft Purview DLP, Strac alternatives: Forcepoint DLP, Nightfall AI, Varonis Data Security Platform
Mistral SmallNetskope DLP alternatives: CurrentWare, Microsoft Purview DLP, Nightfall AI, Safetica, Zscaler Internet Access
DeepSeek V4 FlashNetskope DLP alternatives: Fortra DLP, Next DLP, Nightfall AI
Kimi K2Microsoft Purview DLP alternatives: CurrentWare, Forcepoint DLP, Netwrix Endpoint Protector, Proofpoint Enterprise DLP, miniOrange DLP
GLM 4.7 FlashXMicrosoft Purview DLP alternatives: CrowdStrike Falcon Data Protection, Forcepoint DLP, Netwrix Endpoint Protector, Nightfall AI, Proofpoint Enterprise DLP
Neither was named
8 of 14 modelsThe answer made no first choice from these two in this category.Claude Haiku 4.5Microsoft Purview DLP, Safetica
GPT-5.4 miniMicrosoft Purview DLP alternatives: Forcepoint DLP, Netskope DLP
Grok 4.1 FastMicrosoft Purview DLP alternatives: CurrentWare, Forcepoint DLP, Netwrix Endpoint Protector
Llama 4 Maverickno first choice
Qwen 3.7 FlashNetwrix 1Secure alternatives: Forcepoint DLP, Varonis Data Security Platform
MiniMax M2.5Next DLP
GPT-6 LunaMicrosoft Purview DLP alternatives: Google's native protections for Workspace and Google Cloud, Netskope One
Muse Glimmer 30BSafetica, Safetica ONE alternatives: CurrentWare, Zscaler Internet Access, miniOrange DLP
Bold names in an answer are the products the judge labeled a first choice; a model naming several gives each of them that label. The full answer text for every row is in the record.
By buyer segment
The same question asked on behalf of a different buyer. Each standing is computed within its segment and they are never added together. The figures above are the mid-market standing, which is the one the category orders by.
Small business
Nightfall AI leads by seven points.
Nightfall AI9%#4 of 11Proofpoint Enterprise DLP2%#8 of 11Mid-marketThe figures above
Level: the same share of first choices.
Nightfall AI2%#5 of 15Proofpoint Enterprise DLP2%#8 of 15Enterprise
The order flips: Proofpoint Enterprise DLP leads at enterprise.
Proofpoint Enterprise DLP4%#6 of 11Nightfall AI0%#9 of 11What the models said about Nightfall AI
Every negative label with a quote, up to three, then the highest-weighted positives, up to three. Four of four in this category shown.
“Nightfall AI in the cited review, which is noted as having "no network DLP,"” Perplexity Sonar · negative prompt · soft negative
“Best for SaaS, Cloud Collaboration & GenAI Security: Nightfall AI ... Nightfall is an industry leader.” Gemini 3.5 Flash · direct prompt · first choice
“primarily focuses on providing cloud data loss prevention for generative AI tools, custom applications and Software as a Service applications” Muse Glimmer 30B · comparative prompt · alternative
“Nightfall AI is a cloud-native DLP platform that uses machine learning to protect sensitive data across SaaS applications” Claude Haiku 4.5 · comparative prompt · alternative
What the models said about Proofpoint Enterprise DLP
Every negative label with a quote, up to three, then the highest-weighted positives, up to three. Six of eight in this category shown.
“Enterprise suites (Forcepoint, Symantec, Proofpoint) — typically quote-based and expensive” DeepSeek V4 Flash · budget prompt · hard negative
“can be strong products but are also described as expensive, complex to set up” Perplexity Sonar · negative prompt · soft negative
“Strong email/web protection | Expensive, complex setup” Muse Glimmer 30B · direct prompt · soft negative
“Proofpoint and Forcepoint are top-tier choices due to their comprehensive features and scalability” Mistral Small · paraphrase prompt · first choice
“Excellent for organizations already using Proofpoint for email security.” GLM 4.7 FlashX · direct prompt · alternative
“Best For: Organizations where email leaks are the primary concern” Qwen 3.7 Flash · comparative prompt · alternative
Also compared
Microsoft Purview DLP vs Nightfall AIMicrosoft Purview DLP vs Proofpoint Enterprise DLPSafetica vs Nightfall AISafetica vs Proofpoint Enterprise DLPForcepoint DLP vs Nightfall AIForcepoint DLP vs Proofpoint Enterprise DLPNetskope DLP vs Nightfall AINetskope DLP vs Proofpoint Enterprise DLPNightfall AI vs CurrentWareNightfall AI vs Netwrix Endpoint ProtectorCurrentWare vs Proofpoint Enterprise DLPNetwrix Endpoint Protector vs Proofpoint Enterprise DLPAll twenty-eight head-to-head pages and the full DLP standing
Comparisons are drawn for the top eight products in each category, each against each. The output is the models' output; nothing here is a recommendation by the index.