Email security · November 2026 Edition
Microsoft Defender for Office 365 vs IRONSCALES
Six of fourteen models named Microsoft Defender for Office 365 first on the direct prompt; two named IRONSCALES. Microsoft Defender for Office 365 was named by fourteen of the fourteen models and IRONSCALES by twelve and Microsoft Defender for Office 365 carries 63 labels and IRONSCALES 23, so the shares are not directly comparable.
Named in three categories this edition.
Named in two categories this edition.
First-choice share45%8%Of first choices across the direct, paraphrase, budget and scale prompts, 0 to 100.
Negative rate3%4%Negative labels as a share of the product's labels, 0 to 100.
Rank in category#1#5A position in a field of 9; printed, not drawn.
Labels6323A count; the two differ.
The two percentage rows are drawn on one 0 to 100 track, Microsoft Defender for Office 365 reading right to left. Rank and label count are printed, not drawn.Abnormal AI was named alongside these two in ten of the fourteen direct answers. Microsoft Defender for Office 365 vs Abnormal AI · Microsoft Defender for Office 365 vs Mimecast Email Security · Microsoft Defender for Office 365 vs Check Point Harmony Email & Collaboration
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 email security page.
By framing
How many of the fourteen models made each the first choice, per way of asking, and how many argued against it.
Microsoft Defender for Office 365First choices, of fourteen modelsIRONSCALES
Direct62
Paraphrase91
Comparative50
Budget-constrained70
Scale-constrained211 against Microsoft Defender for Office 365
Negative101 against Microsoft Defender for Office 365 · 1 against IRONSCALES
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 November 2026 Edition, Microsoft Defender for Office 365 and IRONSCALES were named in the same answer fifty-seven times, of the 193 answers naming Microsoft Defender for Office 365 and the 72 naming IRONSCALES. In those answers IRONSCALES took the first choice nine times and Microsoft Defender for Office 365 twenty-one.
Every model, every framing
The eighty-four answers behind the chart above, one cell each: where Microsoft Defender for Office 365 and IRONSCALES 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 4.20 | | | | | | |
| 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 | | | | |
Microsoft Defender for Office 365 IRONSCALES first choice named as an alternative argued againstblank: not namedEach cell is one answer, Microsoft Defender for Office 365 on the left and IRONSCALES on the right.The direct prompt
The plain question, one answer per model, grouped by where Microsoft Defender for Office 365 and IRONSCALES stood in it.
Microsoft Defender for Office 365 first, IRONSCALES an alternative
6 of 14 modelsIRONSCALES was named in the answer but not as the choice, or not at all.GPT-5.4 miniMicrosoft Defender for Office 365, Mimecast Email Security alternatives: Barracuda Email Protection, IRONSCALES, Proofpoint Email Protection
Perplexity SonarMicrosoft Defender for Office 365 alternatives: Abnormal AI, Barracuda Email Protection, Check Point Harmony Email & Collaboration
Grok 4.20Microsoft Defender for Office 365 alternatives: Abnormal AI, Mimecast Email Security, Proofpoint Email Protection
Mistral SmallMicrosoft Defender for Office 365 alternatives: Barracuda Email Protection, Check Point Harmony Email & Collaboration
DeepSeek V4 FlashAbnormal AI, Microsoft Defender for Office 365 alternatives: Hornetsecurity 365 Total Protection, Mimecast Email Security
Llama 4 MaverickMicrosoft Defender for Office 365 alternatives: Barracuda Email Protection, ContentCatcher, SpamTitan
IRONSCALES first, Microsoft Defender for Office 365 an alternative
2 of 14 modelsMicrosoft Defender for Office 365 was named in the answer but not as the choice, or not at all.MiniMax M2.5Check Point Harmony Email & Collaboration, IRONSCALES alternatives: Abnormal AI, Mimecast Email Security, Proofpoint Email Protection
Muse Glimmer 30BIRONSCALES alternatives: Abnormal AI, Barracuda Email Protection, Microsoft Defender for Office 365, Mimecast Email Security, Proofpoint Email Protection
Neither was the first choice, one was named
4 of 14 modelsThe answer put something else first and named one of the two as an alternative.Gemini 3.5 FlashAbnormal AI, Check Point Harmony Email & Collaboration alternatives: Microsoft Defender for Office 365, Mimecast Email Security, Proofpoint Email Protection
Qwen 3.7 FlashProofpoint Email Protection alternatives: Abnormal AI, Check Point Harmony Email & Collaboration, IRONSCALES, Mimecast Email Security
Kimi K2Mimecast Email Security alternatives: Abnormal AI, Barracuda Email Protection, IRONSCALES, Microsoft Defender for Office 365, Proofpoint Email Protection
GPT-6 LunaAbnormal AI alternatives: Check Point Harmony Email & Collaboration, Microsoft Defender for Office 365
Neither was named
2 of 14 modelsThe answer made no first choice from these two in this category.Claude Haiku 4.5no first choice
GLM 4.7 FlashXMimecast Email Security alternatives: Abnormal AI, Barracuda Email Protection, Microsoft Defender XDR, Proofpoint Email Protection
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
Microsoft Defender for Office 365 leads by thirty-one points.
Microsoft Defender for Office 36543%#1 of 10IRONSCALES12%#2 of 10Mid-marketThe figures above
Microsoft Defender for Office 365 leads by thirty-eight points.
Microsoft Defender for Office 36545%#1 of 9IRONSCALES8%#5 of 9Enterprise
Microsoft Defender for Office 365 leads by twenty-four points.
Microsoft Defender for Office 36524%#2 of 10IRONSCALES0%#10 of 10What the models said about Microsoft Defender for Office 365
Every negative label with a quote, up to three, then the highest-weighted positives, up to three. Five of six in this category shown.
“Microsoft 365 users experience 3x more email-related incidents than Google Workspace users” Grok 4.20 · negative prompt · soft negative
“Good value, but many orgs find native M365 needs supplementing.” DeepSeek V4 Flash · scale prompt · soft negative
“Integrated cloud-native solutions: Microsoft Defender for Office 365, Google Workspace security (native integration, no MX changes)” Kimi K2 · negative prompt · first choice
“Best for Microsoft 365 Users: Microsoft Defender for Office 365 (Plan 1) ... often the cheapest path to enterprise-grade features” Gemini 3.5 Flash · budget prompt · first choice
“If I had to pick one default answer: Microsoft Defender for Office 365 if you're Microsoft-centric and want the least friction.” GPT-5.4 mini · direct prompt · first choice
What the models said about IRONSCALES
Every negative label with a quote, up to three, then the highest-weighted positives, up to three. Four of five in this category shown.
“significant drop in recommendation confidence (from 9% to 2%)... indicating potential issues with performance, reliability, or user satisfaction” Mistral Small · negative prompt · hard negative
“Best overall customer satisfaction / AI-native mailbox protection: IRONSCALES. High willingness to recommend and rapid API deployment.” Muse Glimmer 30B · direct prompt · first choice
“I'd suggest starting with either IRONSCALES or Check Point/Avanan” MiniMax M2.5 · direct prompt · first choice
“Start with Proofpoint, Microsoft Defender for Office 365, or IRONSCALES” GLM 4.7 FlashX · scale prompt · first choice
Also compared
Microsoft Defender for Office 365 vs Abnormal AIMicrosoft Defender for Office 365 vs Mimecast Email SecurityMicrosoft Defender for Office 365 vs Check Point Harmony Email & CollaborationMicrosoft Defender for Office 365 vs Proofpoint Email ProtectionMicrosoft Defender for Office 365 vs Barracuda Email ProtectionAbnormal AI vs IRONSCALESMimecast Email Security vs IRONSCALESCheck Point Harmony Email & Collaboration vs IRONSCALESIRONSCALES vs Proofpoint Email ProtectionIRONSCALES vs Barracuda Email ProtectionAll twenty-one head-to-head pages and the full email security 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.