AI Indexes
IT AI Index
Index › Security operations › SSPM › Wing Security vs Obsidian Security
SaaS security posture management · October 2026 Edition

Wing Security vs Obsidian Security

Nine of fourteen models named Wing Security first on the direct prompt; zero named Obsidian Security. Wing Security was named by twelve of the fourteen models and Obsidian Security by thirteen and Wing Security carries 31 labels and Obsidian Security 32, so the shares are not directly comparable.

Wing Security

endorsed leader

Named in one category this edition.

Obsidian Security

accepted challenger

Named in one category this edition.

First-choice share30%4%Of first choices across the direct, paraphrase, budget and scale prompts, 0 to 100.
Negative rate3%9%Negative labels as a share of the product's labels, 0 to 100.
Rank in category#1#5A position in a field of 11; printed, not drawn.
Labels3132A count; the two differ.
The two percentage rows are drawn on one 0 to 100 track, Wing Security reading right to left. Rank and label count are printed, not drawn.Wing Security vs Nudge Security · Wing Security vs Grip Security · Wing Security vs CrowdStrike Falcon Shield

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 saas security posture management page.

By framing

How many of the fourteen models made each the first choice, per way of asking, and how many argued against it.
Wing SecurityFirst choices, of fourteen modelsObsidian Security
Direct901 against Obsidian Security
Paraphrase301 against Wing Security
Comparative02
Budget-constrained321 against Obsidian Security
Scale-constrained10
Negative001 against Obsidian Security
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, Wing Security and Obsidian Security were named in the same answer fifty-one times, of the 87 answers naming Wing Security and the 97 naming Obsidian Security. In those answers Obsidian Security took the first choice six times and Wing Security twenty.

Every model, every framing

The eighty-four answers behind the chart above, one cell each: where Wing Security and Obsidian Security stood in it.
ModelDirectParaphraseComparativeBudget-constrainedScale-constrainedNegative
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
Wing Security Obsidian Security first choice named as an alternative argued againstblank: not namedEach cell is one answer, Wing Security on the left and Obsidian Security on the right.

The direct prompt

The plain question, one answer per model, grouped by where Wing Security and Obsidian Security stood in it.

Wing Security first, Obsidian Security an alternative

9 of 14 modelsObsidian Security was named in the answer but not as the choice, or not at all.
Claude Haiku 4.5Wing Security alternatives: CrowdStrike Shield, Obsidian Security, Spin.AI
Gemini 3.5 FlashWing Security alternatives: CrowdStrike Falcon Shield, Nudge Security, Obsidian Security
Perplexity SonarWing Security alternatives: Obsidian Security, Reco, Spin.AI
Grok 4.1 FastWing Security alternatives: CrowdStrike Falcon Shield, Spin.AI
Qwen 3.7 FlashWing Security alternatives: Adaptive Shield, Grip Security
Kimi K2Wing Security alternatives: Obsidian Security, Valence Security
GLM 4.7 FlashXWing Security alternatives: CrowdStrike Falcon Shield
MiniMax M2.5Wing Security alternatives: AppOmni, BetterCloud, CrowdStrike, Obsidian Security, SpinOne
Muse Glimmer 30BWing Security alternatives: CrowdStrike Falcon Shield, Spin.AI / SpinOne

Neither was the first choice, one was named

1 of 14 modelsThe answer put something else first and named one of the two as an alternative.
DeepSeek V4 FlashAdaptive Shield alternatives: AppOmni, Nudge Security, Wing Security

Neither was named

4 of 14 modelsThe answer made no first choice from these two in this category.
GPT-5.4 miniAppOmni
Mistral SmallGrip Security, Wing alternatives: Nudge Security
Llama 4 Maverickno first choice
GPT-6 LunaValence Security alternatives: CrowdStrike Falcon Shield

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
Wing Security leads by twenty points.
Wing Security20%#2 of 14
Obsidian Security0%#12 of 14
The full small business standing →
Mid-marketThe figures above
Wing Security leads by twenty-six points.
Wing Security30%#1 of 11
Obsidian Security4%#5 of 11
The full mid-market standing →
Enterprise
The order flips: Obsidian Security leads at enterprise.
Obsidian Security6%#3 of 14
Wing Security4%#6 of 14
The full enterprise standing →

What the models said about Wing Security

Every negative label with a quote, up to three, then the highest-weighted positives, up to three. Four of five in this category shown.

“Less depth than Nudge or Obsidian” Kimi K2 · paraphrase prompt · soft negative
“Wing Security stands out as particularly well-suited for mid-market teams due to its balance of affordability, ease of deployment, and practical SaaS discovery capabilities.” Claude Haiku 4.5 · direct prompt · first choice
“Vendors like Wing Security are highly popular for mid-sized organizations because they focus heavily on ease-of-use, low operational overhead” Gemini 3.5 Flash · scale prompt · first choice
“the strongest single pick is Wing Security if you want the best balance of mid-market fit, value, and SaaS discovery” Perplexity Sonar · direct prompt · first choice

What the models said about Obsidian Security

Every negative label with a quote, up to three, then the highest-weighted positives, up to three. Six of seven in this category shown.

“Avoid: Enterprise-focused platforms like ... Obsidian Security” DeepSeek V4 Flash · budget prompt · hard negative
“No built-in remediation or enforcement — identifies threats but doesn't automate response” Kimi K2 · negative prompt · soft negative
“Stronger for enterprise budgets; adds UEBA/behavioral analytics” DeepSeek V4 Flash · direct prompt · soft negative
“Obsidian Security is the strongest budget-friendly starting point because it advertises a $0/month free tier for up to 1,000 users” GPT-5.4 mini · budget prompt · first choice
“Obsidian is currently the standout SaaS vendor for small teams due to its genuinely useful free tier.” GLM 4.7 FlashX · budget prompt · first choice
“Choose AppOmni or Obsidian if you want deep, enterprise-grade SSPM across many SaaS applications.” Perplexity Sonar · comparative prompt · first choice
Also compared
Wing Security vs Nudge SecurityWing Security vs Grip SecurityWing Security vs CrowdStrike Falcon ShieldWing Security vs AppOmniWing Security vs Adaptive ShieldWing Security vs Spin.AINudge Security vs Obsidian SecurityGrip Security vs Obsidian SecurityCrowdStrike Falcon Shield vs Obsidian SecurityObsidian Security vs AppOmniObsidian Security vs Adaptive ShieldObsidian Security vs Spin.AIAll twenty-eight head-to-head pages and the full SSPM 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.