IT AI Index
September 2026 Edition · The permanent record of this edition. The unqualified address always carries the latest edition.
Index › Security operations › Email security › Enterprise › September 2026 Edition

Email security for enterprise buyers

Asked as “email security platform”, and as “phishing and email threat protection tool”, on behalf of an enterprise B2B company. 42 first choices recorded across the direct, paraphrase, budget and scale prompts, twelve models each.
Standing
Proofpoint Email Protection
Clear leader
40% of first choices, clear leader.
ShowinginAll 67 categories in the September 2026 Edition →

By buyer segment

The same question asked on behalf of a different buyer. Each standing is computed within its segment; they sit side by side and are never added together.
Small businessMicrosoft Defender for Office 36544%Clear leaderStanding →Mid-marketMicrosoft Defender for Office 36531%ContestedStanding →EnterpriseProofpoint Email Protection40%Clear leaderThis page

01The standing

Share is the count of first choices across the direct, paraphrase, budget and scale prompts, over all twelve models, for an enterprise B2B company. Ordered by share.
ProductFirst-choice shareNegative rateLabelsQuadrant
01Proofpoint Email Protection40%18%55endorsed leader
02Microsoft Defender for Office 36538%14%50endorsed leader
03Abnormal AI10%17%41accepted challenger
04Mimecast Email Security2%24%49accepted challenger
Show the five products at 0%, ordered by negative rate
09Cisco Secure Email0%35%20criticized challenger
08Barracuda Email Protection0%31%13criticized challenger
07Sublime Security0%9%11accepted challenger
06IRONSCALES0%7%15accepted challenger
05Check Point Harmony Email & Collaboration0%6%17accepted challenger
Bars are the share of first choices, 0 to 100Every product with at least 10 labels here. Every product name links to its vendor page.
Head to head
Microsoft Defender for Office 365 vs Abnormal AIMicrosoft Defender for Office 365 vs Proofpoint Email ProtectionAbnormal AI vs Proofpoint Email Protection

Recommended versus criticized

Every product with at least 10 labels here, on both axes. The 30% line names a quadrant, not the verdict above: that one needs more than 40%.

Criticized challengerCriticized default
Negative label rate →
01
02
03
04
05
06
07
08
09
Accepted challengerEndorsed leader
0%First-choice share → · lines at 30% share and 25% negative60%
Key
01Proofpoint Email Protection40%
02Microsoft Defender for Office 36538%
03Abnormal AI10%
04Mimecast Email Security2%
05Check Point Harmony Email & Collaboration0%
06IRONSCALES0%
07Sublime Security0%
08Barracuda Email Protection0%
09Cisco Secure Email0%

02What they warned about

Three of twelve models held their first choice under the paraphrase. GPT-5.4 mini, Grok 4.1 Fast, Mistral Small, DeepSeek V4 Flash, Llama 4 Maverick, Qwen 3.7 Flash, Kimi K2, GLM 4.7 FlashX and MiniMax M2.5 changed. A high negative share on a product with few labels is a warning. A low share on a product with many labels is salience, not sentiment.
Mimecast Email Security
24%
12 of 49 labels negative · 8 of 12 models · 1 hard negative
“What to Avoid for Predictability - Mimecast — quote-only, opaque pricing” DeepSeek V4 Flash, budget prompt
Proofpoint Email Protection
18%
10 of 55 labels negative · 8 of 12 models
“typically price based on message volume or storage capacity. This creates financial risk... **High** (Charges for overages/API usage)” Qwen 3.7 Flash, budget prompt
Cisco Secure Email
35%
7 of 20 labels negative · 7 of 12 models · 2 hard negative
“Organizations relying on these gateways face high-maintenance patching overhead and increased zero-day exposure.” Gemini 3.5 Flash, negative prompt
Abnormal AI
17%
7 of 41 labels negative · 6 of 12 models
“Quote-only and includes a flat $5K–$15K platform fee plus 5–7% annual renewal uplifts — less transparent for budget planning” DeepSeek V4 Flash, budget prompt

03What they cite

Citations exist only for the models that return a source list: twelve of the twelve in this edition, and all six flagship models on the expanded tier.

Sites the answers cite

62 of 72 answers in this category came back with a source list, from 12 of 12 models: citations where the model returns them, or the search results it consulted. 5 of those lists are Google grounding redirects that name no site and are left out of the counts. 834 links across 191 sites, every framing counted. Ranked by the number of answers carrying the site or page.

gartner.com
41 answers · 48 citations · 11 models
sublime.security
vendor site · Sublime33 answers · 46 citations · 10 models
expertinsights.com
vendor site · Expert Insights26 answers · 38 citations · 10 models
tech-insider.org
26 answers · 29 citations · 9 models
proofpoint.com
vendor site · Proofpoint25 answers · 55 citations · 8 models
kaseya.com
vendor site · Kaseya21 answers · 21 citations · 9 models
learn.g2.com
18 answers · 18 citations · 10 models
costbench.com
17 answers · 23 citations · 9 models
cipherssecurity.com
17 answers · 20 citations · 9 models
powerdmarc.com
14 answers · 14 citations · 6 models
huntress.com
vendor site · Huntress13 answers · 14 citations · 7 models
bcs365.com
13 answers · 13 citations · 7 models

Pages the answers cite

The ten pages named in the most answers, by full address. A page here is one the models returned with a recommendation, not one the index endorses.

gartner.com/reviews/market/email-security
40 answers · 10 models
sublime.security/articles/enterprise-email-security-solutions
29 answers · 10 models
expertinsights.com/email-security/top-email-security-gateways
23 answers · 10 models
kaseya.com/blog/best-email-security-solutions
21 answers · 9 models
learn.g2.com/best-cloud-email-security-platforms
18 answers · 10 models
costbench.com/best/best-email-security-for-enterprise
16 answers · 9 models
tech-insider.org/proofpoint-vs-abnormal-vs-mimecast-2026
16 answers · 8 models
cipherssecurity.com/best-email-security-gateways-2026
15 answers · 9 models
bcs365.com/insights/best-email-security-solutions-gartner
13 answers · 7 models
guptadeepak.com/tools/top-5-email-security-platforms-2026
12 answers · 9 models

04How they answered

Six framings of the same buying question, each sent to every model in a fresh session with search on. One row per model, so a row shows whether it held its answer under rewording, what it named when cost was the constraint, and what it argued against. Computed from the raw judge labels.
ModelDirect“What is the best email security platform for an enterprise B2B company?”Paraphrase“Which phishing and email threat protection tool would you recommend to a large B2B company with thousands of employees?”Comparative“What are the top enterprise-grade email security platforms and how do they differ?”Budget-constrained“What is the best email security platform for a large company that needs predictable total cost across thousands of users?”Scale-constrained“We are a 5,000 person company with SSO, SOC 2 and procurement review requirements evaluating an email security platform. What should we look at?”Negative“Which email security platforms should a large enterprise avoid or be cautious about?”
Claude Haiku 4.5Proofpoint Email Protection
Two alternativesAbnormal AI, Mimecast Email Security
Proofpoint Email ProtectionHeld
Three alternativesAbnormal AI, IRONSCALES, Mimecast Email Security
Proofpoint Email Protection
Four alternativesAbnormal AI, IRONSCALES, Microsoft Defender for Office 365, Mimecast Email Security
Microsoft Defender for Office 365
Two alternativesCoro, IRONSCALES
no first choiceagainst: Cisco Secure Email, Exchange Server, SmarterMail
GPT-5.4 miniMicrosoft Defender for Office 365
Two alternativesMimecast Email Security, Proofpoint Email Protection
Proofpoint Email ProtectionChanged
Two alternativesAbnormal AI, Microsoft Defender for Office 365
Microsoft Defender for Office 365
Three alternativesGoogle Workspace, Mimecast Email Security, Proofpoint Email Protection
Microsoft Defender for Office 365
One alternativeProofpoint Email Protection
no first choicenothing named
Gemini 3.5 FlashAbnormal AI
Six alternativesCheck Point Harmony Email & Collaboration, IRONSCALES, Microsoft Defender for Office 365, Mimecast Email Security, Proofpoint Email Protection, Sublime Security
Abnormal AIHeld
Five alternativesCheck Point Harmony Email & Collaboration, Google Workspace, Microsoft Defender for Office 365, Proofpoint Email Protection, Sublime Security
Abnormal AI, Sublime Security
Four alternativesCheck Point Harmony Email & Collaboration, Microsoft Defender for Office 365, Mimecast Email Security, Proofpoint Email Protection
Microsoft Defender for Office 365
Two alternativesCheck Point Harmony Email & Collaboration, Cloudflare Area 1 Email Security
against: Abnormal AI, Mimecast Email Security, Proofpoint Email Protectionno first choiceagainst: Cisco Secure Email, Google Workspace, Microsoft 365, Symantec Email Security.cloud
Perplexity SonarProofpoint Email Protection
Three alternativesAbnormal AI, Barracuda Email Protection, Mimecast Email Security
Proofpoint Email ProtectionHeld
Three alternativesAbnormal AI, IRONSCALES, Microsoft Defender for Office 365
Proofpoint Email Protection
Four alternativesAbnormal AI, Check Point Harmony Email & Collaboration, Microsoft Defender for Office 365, Mimecast Email Security
Microsoft Defender for Office 365, SpamTitanagainst: Mimecast Email Security, Proofpoint Email Protectionno first choiceagainst: Abnormal AI, Check Point Harmony Email & Collaboration, Cisco Secure Email, Guardz, IRONSCALES, MailWasher, Mailfence, Material Security, Proton Mail, SpamTitan, Trustifi, Tuta
Grok 4.1 FastMicrosoft Defender for Office 365, Proofpoint Email Protection
Two alternativesAbnormal AI, Mimecast Email Security
Proofpoint Email ProtectionChanged
Two alternativesAbnormal AI, Mimecast Email Security
against: Microsoft Defender for Office 365Proofpoint Email Protection
Three alternativesAbnormal AI, Check Point Harmony Email & Collaboration, Mimecast Email Security
against: Microsoft Defender for Office 365Microsoft Defender for Office 365
One alternativeProofpoint Email Protection
against: Abnormal AI, Mimecast Email Securityno first choiceagainst: Barracuda Email Protection, Cisco Secure Email, Darktrace, Hornetsecurity, Microsoft Defender for Office 365, Mimecast Email Security, Proofpoint Email Protection, Symantec Email Security.cloud
Mistral SmallMicrosoft Defender for Office 365, Proofpoint Email Protection
Two alternativesAbnormal AI, Mimecast Email Security
NetcraftChanged
Three alternativesCloudflare Area 1 Email Security, Mimecast Email Security, Proofpoint Email Protection
Proofpoint Email Protection
Three alternativesAbnormal AI, Microsoft Defender for Office 365, Mimecast Email Security
Proofpoint Email Protection
One alternativeMicrosoft Defender for Office 365
against: Mimecast Email Securityno first choiceagainst: Barracuda Email Security Gateway, Cisco Secure Email, Mimecast Email Security, Proofpoint Email Protection
DeepSeek V4 FlashAbnormal AI
Three alternativesMicrosoft Defender for Office 365, Mimecast Email Security, Proofpoint Email Protection
Proofpoint Email ProtectionChanged
One alternativeAbnormal AI
against: Mimecast Email SecurityProofpoint Email Protection
Three alternativesAbnormal AI, Microsoft Defender for Office 365, Mimecast Email Security
Barracuda Email Security Gateway
One alternativeMicrosoft Defender for Office 365
against: Abnormal AI, Mimecast Email Security, Proofpoint Email Protectionno first choiceagainst: Abnormal AI, Barracuda Email Protection, Cisco Secure Email, Darktrace EMAIL, Fortra (formerly HelpSystems) / Agari, Google Workspace, Microsoft Defender for Office 365, Mimecast Email Security, Sublime Security, Symantec Email Security.cloud
Llama 4 Maverickno first choiceMicrosoft Defender for Office 365Changed
Two alternativesCheck Point Harmony Email & Collaboration, PowerDMARC
no first choiceProofpoint Email Protection
Two alternativesMicrosoft Defender for Office 365, Mimecast Email Security
no first choicenothing named
Qwen 3.7 FlashMicrosoft Defender for Office 365, Proofpoint Email Protection
Two alternativesAbnormal AI, Mimecast Email Security
Abnormal AIChanged
Two alternativesMimecast Email Security, Proofpoint Email Protection
against: Microsoft Defender for Office 365no first choiceMicrosoft Defender for Office 365, Zix
One alternativeNucleus Cyber
against: Mimecast Email Security, Proofpoint Email Protectionno first choiceagainst: Barracuda Email Security Gateway, Proofpoint Email Protection
Kimi K2Mimecast Email Security, Proofpoint Email Protection
One alternativeMicrosoft Defender for Office 365
Proofpoint Email ProtectionChanged
Three alternativesAbnormal AI, Microsoft Defender for Office 365, Mimecast Email Security
no first choice
Seven alternativesAbnormal AI, Cisco Secure Email, IRONSCALES, Microsoft Defender for Office 365, Mimecast Email Security, Proofpoint Email Protection, Sublime Security
against: Barracuda Email ProtectionMicrosoft Defender for Office 365
One alternativeMimecast Email Security
against: Abnormal AI, Proofpoint Email Protectionno first choiceagainst: Barracuda Email Security Gateway, Cisco Secure Email, Microsoft Native Email Security Alone, Mimecast Email Security, Proofpoint Email Protection
GLM 4.7 FlashXMicrosoft Defender for Office 365, Proofpoint Email Protection
Four alternativesAbnormal AI, Barracuda Email Protection, Cisco Secure Email, Mimecast Email Security
Proofpoint Email ProtectionChanged
Five alternativesAbnormal AI, Barracuda Email Protection, Cisco Secure Email, Microsoft Defender for Office 365, Mimecast Email Security
Microsoft Defender for Office 365
Eight alternativesBarracuda Email Security Gateway, Cisco Secure Email, Google Workspace, Mimecast Email Security, Proofpoint Email Protection, Sophos Email, Tessian, Zix
Microsoft Defender for Office 365
Three alternativesAbnormal AI, Mimecast Email Security, Proofpoint Email Protection
no first choicenothing named
MiniMax M2.5Microsoft Defender for Office 365
Two alternativesMimecast Email Security, Proofpoint Email Protection
Proofpoint Email ProtectionChanged
One alternativeMimecast Email Security
against: Microsoft Defender for Office 365no first choice
Four alternativesAbnormal AI, Mimecast Email Security, Proofpoint Email Protection, Sublime Security
against: Microsoft Defender for Office 365Microsoft Defender for Office 365against: Abnormal AIno first choiceagainst: Barracuda Email Protection, Google Workspace, Microsoft 365, Mimecast Email Security, Proofpoint Email Protection
Bold is the first choiceAlternatives are counted; the count opens them.What the answer argued against

05The record

One row per call: the version string exactly as returned, whether the model searched, sources cited, and latency. Full answer text is in the free responses file. Download the record
Seventy-two rows: every prompt, every model, every answer.
PromptModelVersion stringTime (UTC)SearchedSourcesLatency
Direct recommendationClaude Haiku 4.5claude-haiku-4-5-202510012026-09-17 12:46yes98 s
Direct recommendationGPT-5.4 minigpt-5.4-mini-2026-03-172026-09-17 10:18yes25 s
Direct recommendationGemini 3.5 Flashgemini-3.5-flash2026-09-17 09:25yes1824 s
Direct recommendationPerplexity Sonarsonar2026-09-17 13:54yes205 s
Direct recommendationGrok 4.1 Fastspacexai/grok-4.1-fast-non-reasoning via vertex2026-09-17 13:05yes1710 s
Direct recommendationMistral Smallmistral/mistral-small via mistral2026-09-17 11:21yes78 s
Direct recommendationDeepSeek V4 Flashdeepseek/deepseek-v4-flash via fireworks2026-09-17 12:08yes1814 s
Direct recommendationLlama 4 Maverickmeta/llama-4-maverick via bedrock2026-09-17 13:11yes53 s
Direct recommendationQwen 3.7 Flashalibaba/qwen3.7-flash via alibaba2026-09-17 13:08yes1043 s
Direct recommendationKimi K2moonshotai/kimi-k2 via novita2026-09-17 09:57yes1028 s
Direct recommendationGLM 4.7 FlashXzai/glm-4.7-flashx via zai2026-09-17 12:07yes29142 s
Direct recommendationMiniMax M2.5minimax/minimax-m2.5 via minimax2026-09-17 12:11yes518 s
ParaphraseClaude Haiku 4.5claude-haiku-4-5-202510012026-09-17 13:38yes189 s
ParaphraseGPT-5.4 minigpt-5.4-mini-2026-03-172026-09-17 10:35yes36 s
ParaphraseGemini 3.5 Flashgemini-3.5-flash2026-09-17 12:21yes1526 s
ParaphrasePerplexity Sonarsonar2026-09-17 13:15yes205 s
ParaphraseGrok 4.1 Fastspacexai/grok-4.1-fast-non-reasoning via vertex2026-09-17 11:19yes199 s
ParaphraseMistral Smallmistral/mistral-small via mistral2026-09-17 14:11yes55 s
ParaphraseDeepSeek V4 Flashdeepseek/deepseek-v4-flash via fireworks2026-09-17 13:28yes2021 s
ParaphraseLlama 4 Maverickmeta/llama-4-maverick via bedrock2026-09-17 12:45yes53 s
ParaphraseQwen 3.7 Flashalibaba/qwen3.7-flash via alibaba2026-09-17 14:05no037 s
ParaphraseKimi K2moonshotai/kimi-k2 via novita2026-09-17 11:15yes1732 s
ParaphraseGLM 4.7 FlashXzai/glm-4.7-flashx via zai2026-09-17 10:42yes20131 s
ParaphraseMiniMax M2.5minimax/minimax-m2.5 via minimax2026-09-17 10:44yes1337 s
ComparativeClaude Haiku 4.5claude-haiku-4-5-202510012026-09-17 13:39yes910 s
ComparativeGPT-5.4 minigpt-5.4-mini-2026-03-172026-09-17 10:49yes711 s
ComparativeGemini 3.5 Flashgemini-3.5-flash2026-09-17 10:00yes1926 s
ComparativePerplexity Sonarsonar2026-09-17 09:23yes208 s
ComparativeGrok 4.1 Fastspacexai/grok-4.1-fast-non-reasoning via vertex2026-09-17 13:56yes2418 s
ComparativeMistral Smallmistral/mistral-small via mistral2026-09-17 09:37yes1012 s
ComparativeDeepSeek V4 Flashdeepseek/deepseek-v4-flash via fireworks2026-09-17 14:06yes1928 s
ComparativeLlama 4 Maverickmeta/llama-4-maverick via bedrock2026-09-17 13:15yes53 s
ComparativeQwen 3.7 Flashalibaba/qwen3.7-flash via alibaba2026-09-17 09:58yes526 s
ComparativeKimi K2moonshotai/kimi-k2 via novita2026-09-17 14:15yes1879 s
ComparativeGLM 4.7 FlashXzai/glm-4.7-flashx via zai2026-09-17 13:21no038 s
ComparativeMiniMax M2.5minimax/minimax-m2.5 via minimax2026-09-17 10:19yes521 s
Budget constrainedClaude Haiku 4.5claude-haiku-4-5-202510012026-09-17 12:59yes159 s
Budget constrainedGPT-5.4 minigpt-5.4-mini-2026-03-172026-09-17 11:02yes46 s
Budget constrainedGemini 3.5 Flashgemini-3.5-flash2026-09-17 10:41yes2432 s
Budget constrainedPerplexity Sonarsonar2026-09-17 13:34yes205 s
Budget constrainedGrok 4.1 Fastspacexai/grok-4.1-fast-non-reasoning via vertex2026-09-17 09:37yes2917 s
Budget constrainedMistral Smallmistral/mistral-small via mistral2026-09-17 10:08yes55 s
Budget constrainedDeepSeek V4 Flashdeepseek/deepseek-v4-flash via fireworks2026-09-17 11:19yes1921 s
Budget constrainedLlama 4 Maverickmeta/llama-4-maverick via bedrock2026-09-17 14:09yes53 s
Budget constrainedQwen 3.7 Flashalibaba/qwen3.7-flash via alibaba2026-09-17 09:47no033 s
Budget constrainedKimi K2moonshotai/kimi-k2 via novita2026-09-17 09:32yes1962 s
Budget constrainedGLM 4.7 FlashXzai/glm-4.7-flashx via zai2026-09-17 13:45yes1369 s
Budget constrainedMiniMax M2.5minimax/minimax-m2.5 via minimax2026-09-17 12:43yes1655 s
Scale constrainedClaude Haiku 4.5claude-haiku-4-5-202510012026-09-17 09:48no011 s
Scale constrainedGPT-5.4 minigpt-5.4-mini-2026-03-172026-09-17 13:29no08 s
Scale constrainedGemini 3.5 Flashgemini-3.5-flash2026-09-17 13:14no015 s
Scale constrainedPerplexity Sonarsonar2026-09-17 10:24yes2014 s
Scale constrainedGrok 4.1 Fastspacexai/grok-4.1-fast-non-reasoning via vertex2026-09-17 13:18yes1914 s
Scale constrainedMistral Smallmistral/mistral-small via mistral2026-09-17 13:15no08 s
Scale constrainedDeepSeek V4 Flashdeepseek/deepseek-v4-flash via fireworks2026-09-17 13:10yes2326 s
Scale constrainedLlama 4 Maverickmeta/llama-4-maverick via bedrock2026-09-17 14:11yes55 s
Scale constrainedQwen 3.7 Flashalibaba/qwen3.7-flash via alibaba2026-09-17 11:27no039 s
Scale constrainedKimi K2moonshotai/kimi-k2 via novita2026-09-17 10:28yes867 s
Scale constrainedGLM 4.7 FlashXzai/glm-4.7-flashx via zai2026-09-17 11:34yes1482 s
Scale constrainedMiniMax M2.5minimax/minimax-m2.5 via minimax2026-09-17 13:10no064 s
Negative framingClaude Haiku 4.5claude-haiku-4-5-202510012026-09-17 12:34yes189 s
Negative framingGPT-5.4 minigpt-5.4-mini-2026-03-172026-09-17 11:28no04 s
Negative framingGemini 3.5 Flashgemini-3.5-flash2026-09-17 11:11yes1325 s
Negative framingPerplexity Sonarsonar2026-09-17 10:14yes208 s
Negative framingGrok 4.1 Fastspacexai/grok-4.1-fast-non-reasoning via vertex2026-09-17 09:36yes2714 s
Negative framingMistral Smallmistral/mistral-small via mistral2026-09-17 13:51yes2420 s
Negative framingDeepSeek V4 Flashdeepseek/deepseek-v4-flash via fireworks2026-09-17 09:23yes2862 s
Negative framingLlama 4 Maverickmeta/llama-4-maverick via bedrock2026-09-17 14:11yes53 s
Negative framingQwen 3.7 Flashalibaba/qwen3.7-flash via alibaba2026-09-17 12:45yes1054 s
Negative framingKimi K2moonshotai/kimi-k2 via novita2026-09-17 13:59yes2574 s
Negative framingGLM 4.7 FlashXzai/glm-4.7-flashx via zai2026-09-17 13:10yes2727 s
Negative framingMiniMax M2.5minimax/minimax-m2.5 via minimax2026-09-17 10:01yes2267 s

Normalization in this category

Every judgment call made between the raw labels and the numbers above, listed so it is visible and reversible.

Category-scoped readings
Abnormal read as Abnormal AI
Barracuda read as Barracuda Email Protection
Barracuda (Email Security Gateway - ESG) read as Barracuda Email Protection
Check Point read as Check Point Harmony Email & Collaboration
Check Point (Avanan) read as Check Point Harmony Email & Collaboration
Check Point Harmony Email read as Check Point Harmony Email & Collaboration
Cisco read as Cisco Secure Email
Google Workspace Security read as Google Workspace
Google Workspace security read as Google Workspace
Microsoft Defender read as Microsoft Defender for Office 365
Mimecast read as Mimecast Email Security
Mimecast (Advanced Email Security) read as Mimecast Email Security
Proofpoint read as Proofpoint Email Protection
Proofpoint (Threat Protection Platform) read as Proofpoint Email Protection
Proofpoint Enterprise read as Proofpoint Email Protection
Proofpoint Essentials read as Proofpoint Email Protection
Sophos read as Sophos Email
Unresolved, counted raw
Exchange Server
Fortra (formerly HelpSystems) / Agari
MailMarshal
MailWasher
Microsoft Native Email Security Alone
Mimecast's newer behavioral modules
Netcraft
Nucleus Cyber
PowerDMARC
SmarterMail
Discontinued, still offered
No shut-down product was recommended here.

Also in security operations

The other categories of this function, with the leader in each.
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