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REVIEW 4 major objections 5 minor 98 references

Measuring and Augmenting Large Language Models for Solving Capture-the-Flag Challenges

T0 review · 4 major / 5 minor · reviewed 2026-08-06 · deepseek-v4-flash

Pith's one-line read LLMs know CTF theory but fail to apply it; a two-stage retrieval and an interactive shell close most of the gap.

desk verdict CTFKnow is a real benchmark, but the agent evaluation leaks test-solution payloads through its own RAG database, so the headline 85%/120% gains don't stand. read the letter →

arxiv 2506.17644 v1 pith:U52ITS5N submitted 2025-06-21 cs.AI

classification cs.AI
keywords Capture-the-FlagLLMbenchmarkretrieval-augmentedgenerationoffensivesecurityagentsCTFautomationknowledgeapplication
verification ladder T0 review T1 audit T2 compute T3 formal

The pith

A machine-rendered reading of the paper's core claim, the machinery that carries it, and where it could break.

The reading

This paper argues that what blocks large language models from solving Capture-the-Flag challenges is not missing technical knowledge but the application of that knowledge to concrete scenarios and the ability to act on feedback from the environment. To show this, the authors build CTFKnow, a 3,992-question benchmark of single-choice and open-ended questions distilled from over a thousand CTF write-ups, and measure five LLMs. The measurement finds that LLMs answer around 80 percent of single-choice questions but drop by roughly half on open-ended questions, and that they degrade further as challenge difficulty rises. The paper then proposes CTFAgent, which pairs a two-stage retrieval-augmented generation module with an interactive environment module, and reports that it raises solved challenges from 39 to 73 out of 100 on Intercode-CTF, from 8 to 18 out of 200 on the NYU CTF Dataset, and reaches the top 23.6 percent of nearly 7,000 teams in picoCTF2024.

What carries the argument

The operating mechanism is the two-stage RAG pipeline. RAG-Understanding takes the code the agent reads from the challenge files, embeds it, and returns the two most similar vulnerability knowledge trunks; RAG-Exploiting takes each exploit idea the model proposes, embeds it, and returns the closest exploit-method knowledge, often including a ready-made payload. The interactive Environmental Augmentation module complements this by giving the model persistent netcat sessions with immediate, line-by-line feedback, prebuilt tool-use hints, and a modern decompiler, so that retrieved knowledge can actually be executed and corrected. CTFKnow, the measurement benchmark, is built by extracting 2,078 knowledge points from 1,084 write-ups with GPT-4, filtering them with a different LLM, and generating paired single-choice and open-ended questions, with 323 items manually verified at 99.38 percent accuracy.

What would settle it

A concrete falsifier is a temporal split evaluation: build the RAG database only from write-ups published before 2023, run CTFAgent on the 2024 picoCTF and the newest Intercode-CTF challenges, and check whether the solve rate drop is large. If the drop is large, the reported gains measure retrieval from a corpus that overlaps the test set rather than CTF capability; if the drop is small, the two-stage RAG transfers general technique and the claim survives. A second check is to count how many CTFAgent solutions contain payload strings verbatim identical to RAG database entries rather than semantically equivalent variants.

Watch

Extended reading notes

Core claim

The central claim is that LLMs already possess most of the technical knowledge needed for CTF challenges, but they fail to match that knowledge to specific scenarios and to adapt their actions based on environment feedback. The paper supports this with CTFKnow, which separates knowledge recall (single-choice) from knowledge application (open-ended), and with CTFAgent, which supplies the missing pieces: a two-stage RAG that retrieves vulnerability-identification hints from code snippets in the understanding phase and exploit-knowledge hints from the model's own exploit ideas in the exploiting phase, plus an interactive environment with real-time netcat sessions, tool-use hints, and upgraded decompilation. The paper reports that this combination improves end-to-end solving by 85 percent on Intercode-CTF and by more than 120 percent on the NYU CTF Dataset, and that the gains concentrate in challenges that previously required long, multi-round interactions.

Load-bearing premise

The paper assumes that the CTF write-up corpus used to build the RAG database does not effectively contain the answers to the test challenges; for at least one test challenge the figure showing the pipeline returns the exact exploit payload suggests this assumption may be violated at a level that could inflate the reported solve rates.

Editorial extensions

If this is right

  • If the 85 percent gain is real, then external knowledge retrieval plus an interactive execution environment is the main lever for turning LLMs into competent CTF solvers, and other benchmarks should be redesigned to include both.
  • The less-than-50 percent performance on open-ended questions implies that knowledge recall benchmarks overstate readiness: any evaluation of LLMs for offensive security should test application, not just recognition.
  • The finding that the baseline solved no challenges beyond round four while CTFAgent solved some after twenty rounds suggests that preserving context and maintaining a session over many turns is itself a bottleneck that future agents need to address.
  • The picoCTF2024 result, with CTFAgent beating the NYU framework's rank by nearly half, implies that a RAG-plus-environment design can transfer from curated datasets to a live competition without special adaptation.
  • Because CTFAgent's RAG retrieves from the same write-up ecosystem that produced the test challenges, the reported gains should be read as the upper bound of what retrieval support can do, not as a measure of unaided reasoning.

Reading between the lines

Editorial extensions of the paper, not claims the author makes directly.

  • A direct test of whether the RAG database is leaking solutions would be to rebuild the knowledge base from write-ups that postdate the test challenges and rerun the evaluation; if gains persist, the two-stage retrieval is genuinely transferring technique rather than memorized answers.
  • The gap between single-choice and open-ended accuracy suggests that the same measurement design could be applied to other skill domains where LLMs look capable on multiple-choice tests but falter in practice, such as penetration testing or secure code review.
  • One could extend CTFAgent by feeding the final successful payload back into the RAG database as a new knowledge trunk, turning each solved challenge into a reusable exploit template; the paper does not propose this self-expanding loop.
  • The failure analysis's observation that models emit irrelevant content instead of retrying after a failed approach points to a testable fix: an output filter that detects non-task text and forces the agent to emit a concrete next action, which would likely push the solve rate higher on both datasets.
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Editorial analysis

A structured set of objections, weighed in public.

Desk editor's note, referee report, and a circularity audit.

Referee Report

4 major / 5 minor

Summary. The paper makes two contributions: (1) CTFKnow, a benchmark of 1,996 technical knowledge points and 3,992 single-choice/open-ended questions built from 1,084 CTF write-ups, used to measure LLMs' CTF knowledge and its application; and (2) CTFAgent, an LLM agent with two-stage RAG and interactive Environmental Augmentation, claimed to improve solved challenges by 85% on Intercode-CTF (39/100 to 73/100) and by 120% on NYU CTF (8/200 to 18/200), plus a top-23.6% ranking at picoCTF2024. The measurement study finds that LLMs perform well on single-choice CTF knowledge questions but much worse on open-ended application questions. The central empirical claim about CTFAgent is not supportable as presented because the RAG corpus is constructed from write-ups of the same competitions used for testing, with at least one documented case of retrieving the exact exploit payload for a test challenge; additional confounds include unmatched interaction-round budgets and an uncontrolled NYU baseline.

Significance. If the CTFAgent results were valid, the paper would make a substantial contribution: it would demonstrate that targeted retrieval and environment improvements can turn LLMs into credible automatic CTF solvers, and CTFKnow would be a useful benchmark for isolating technical knowledge from reasoning in security tasks. The CTFKnow construction pipeline is a genuine strength: it includes LLM-based knowledge extraction and filtering, a second-model cross-check, and manual verification of 323 sampled items. However, the framework evaluation is the load-bearing part of the paper, and its central numbers are compromised by test-set contamination and uncontrolled comparisons. The significance of the work therefore cannot be assessed from the reported experiments; the paper would need a substantially decontaminated and controlled evaluation to support its claims.

major comments (4)
  1. [§3.2, §4.2, §5.1, Figure 8] The RAG database directly overlaps with the test sets. The corpus is built from CTFtime write-ups of 'over 700 large-scale international CTF competitions' (§3.2), and the two evaluation datasets are picoCTF (Intercode-CTF) and CSAW (NYU CTF) challenges, both of which are exactly the type of competitions documented on CTFtime. §5.1 states that CTFKnow is already maintained in CTFAgent's RAG system, so the retrieval database also incorporates the 1,084 write-ups used to build CTFKnow. Figure 8, presented as the workflow example for the CSAW test challenge 'puffin', shows DB-Exploiting returning the exact payload 'A'x16 . 'B'x4 . 'C'x108 as a hint, i.e., the solution to that test challenge. The paper reports no decontamination step, such as excluding write-ups for the specific test challenges from the retrieval corpus. Consequently, the reported gains from 39 to 73 on Intercode-CTF and from 8 to 18 on NYU CTF can be explained by retrieval of solution write-ups rather than by the proposed modules. This issue is load-bearing for the paper's central claim and must be resolved before the results can be interpreted.
  2. [§5.3] The ablation design cannot distinguish knowledge augmentation from answer retrieval. Removing RAG entirely (CTFAgent-w/o-RAG) also removes the contaminated retrieval channel, so the performance gap between CTFAgent and CTFAgent-w/o-RAG in Tables 2 and 3 measures how often the database contains a solution to the test challenge, not the marginal value of the two-stage RAG mechanism. A proper ablation should keep the retrieval channel intact while using a decontaminated corpus (e.g., excluding write-ups originating from the same competitions or the same challenge names), or an unrelated control corpus, so that the retrieval process is exercised without leaking test solutions.
  3. [§5.1, Figure 9] The interaction-round budget is not matched between the compared systems. §5.1 sets CTFAgent's maximum interaction rounds to 30 for both datasets, while Figure 9 shows the Intercode baseline solving no challenges beyond the fourth round. If the baseline is capped at a much smaller number of rounds, the comparison conflates the effect of the two modules with the effect of a substantially larger action budget. The authors should either grant the baseline the same 30-round budget or report solve rates at a common round limit. This confound applies independently of the contamination issue.
  4. [Table 3] The NYU CTF baseline is not evaluated in a controlled setting. The note under Table 3 states, 'We obtained experimental data of NYU CTF directly from the paper by Shao et al. [71].' This means the model version, tooling, environment, and execution protocol are not matched between CTFAgent and the NYU baseline, so the claimed 120% improvement rests on an externally reported number rather than a head-to-head comparison. The same concern applies to the picoCTF2024 comparison in Table 5, where no evidence is provided that the NYU framework was run under identical conditions by the same pipeline.
minor comments (5)
  1. [§3.2] The text reports 'over 700 large-scale international CTF competitions' and 'over 10,000 write-ups,' yet after filtering only 1,084 write-ups remain; please clarify whether the 700-competition and 10,000-write-up figures refer to the raw scrape and explain how the filtered set is distributed across competitions.
  2. [Figure 8] The final panel shows 'casw{...}' as the flag, while the text states the flag format is 'csawctf{....}'; this typo should be corrected.
  3. [§1] The word 'disscussed' appears in the Introduction and should be 'discussed'.
  4. [Table 1] The human evaluation row is based on a small sampled subset (90 single-choice and 30 open-ended questions per participant) with different open-ended scoring procedures than the LLM evaluation; please state the variance or confidence intervals so the human-LLM comparison is not over-interpreted.
  5. [§5.2, Table 4] The o1-preview evaluation is only run on challenges unsolved by GPT-4-Turbo, and the statement that challenges solved by GPT-4-Turbo 'can be readily addressed by the o1 model' is not demonstrated by any reported run; please qualify this claim or provide the supporting data.

Circularity Check

1 steps flagged · score 6.0 of 10

Reported CTFAgent gains are partially circular: the RAG knowledge base is built from write-ups of the same competitions as the test sets, and Figure 8 shows a test challenge's exact exploit payload being retrieved from DB-Exploiting, so the 39-to-73 and 8-to-18 improvements are not shown to exceed stored-solution retrieval.

  1. other [§2.1, §3.2, §5.1, §4.4 and Figure 8]
    "In this paper, all collected write-ups have been sourced from CTFtime. ... We first select over 700 large-scale international CTF competitions from the past five years ... To clarify, we do not use CTFKnow here, as it is designed for measuring LLMs' knowledge acquisition ability (and it is already maintained in CTFAgent's RAG system), not for evaluating their end-to-end CTF solving ability. ... When RAG's DB-Exploit receives this idea, it searches its database for the most closely related piece of technical knowledge, which includes an example payload for buffer overflow. ..."

    The RAG corpus is CTFKnow, assembled from CTFtime write-ups of competitions that include the evaluation ecosystems: Intercode-CTF is a picoCTF collection and NYU CTF is a CSAW collection. The paper never reports a holdout removing write-ups whose challenges appear in the test sets. Figure 8 demonstrates the mechanism concretely: for the NYU CSAW test challenge 'puffin', DB-Exploiting returns the exact exploit payload ('A'x16 . 'B'x4 . 'C'x108). A solved challenge can therefore be a retrieval of a stored solution rather than a capability produced by the proposed two-stage RAG and Environmental Augmentation. The ablation variant 'CTFAgent-w/o-RAG' removes the contaminated retrieval channel, so the gaps in Tables 2 and 3 (39 to 73, 8 to 18) measure corpus overlap as much as framework value.

full rationale

The strongest evidence of circularity is provenance overlap between the RAG database and the evaluation sets, confirmed by the paper's own Figure 8: a test challenge ('puffin' from NYU CSAW) receives its exact exploit payload from DB-Exploiting. Because CTFKnow is described as 'already maintained in CTFAgent's RAG system' and is built from CTFtime write-ups of over 700 competitions, the evaluation does not establish that the proposed modules generalize beyond stored-solution lookup. This makes the headline performance gain partially circular, even though the RAG module also supplies generic knowledge that could aid unrelated challenges. The CTFKnow measurement study itself (single-choice and open-ended knowledge questions) is largely self-contained and does not rely on self-citation chains; findings about knowledge recall versus scenario-matching have independent content. The unmatched round budgets visible in Figure 9 (baseline solving nothing after round 4 while CTFAgent uses up to 30 rounds) are an additional confound affecting internal validity, but they are a comparison-protocol issue rather than a circularity of the derivation chain. Because only one concrete contamination case is exhibited and the paper does not quantify corpus overlap, the circularity is substantial but not total: score 6 rather than 8 or 10.

Assumptions & free parameters 5 free parameters · 5 assumptions · 0 invented entities

The central claims rest on five hand-chosen settings (top-k, rounds, extraction limit, filter threshold, sample size) and on several domain assumptions about benchmark validity, judge neutrality, and evaluation fairness. The most fragile assumption is that the RAG database does not contain write-ups of the test challenges, which Figure 8 directly contradicts. No new physical or mathematical entities are postulated; CTFAgent's modules are software components, not invented entities in the sense of this ledger.

free parameters (5)
  • RAG top-k = 2
    Two most related knowledge pieces returned as hints (Figure 7, §4.2); no sensitivity analysis reported.
  • Max interaction rounds = 30
    30 rounds for CTFAgent on both datasets (§5.1); baseline max rounds not reported, so gains may partly reflect longer budget.
  • Knowledge points per write-up = up to 2
    Prompt instructs GPT-4 to extract up to 2 knowledge points per write-up (§3.2 step 2), limiting benchmark coverage.
  • DeepSeek filtering threshold = score 5
    Only knowledge points scored 5 ('fully matches') are kept (§3.2 step 3 and Appendix C).
  • Manual verification sample size = 323
    Used to claim 99.38% reliability; a random sample, but only two inaccuracies found (§3.2 step 5).
assumptions (5)
  • domain assumption LLM-extracted and LLM-filtered knowledge points accurately reflect the original write-ups.
    Benchmark validity depends on GPT-4 extraction and DeepSeek filtering being accurate; only 323 of 1,996 instances were manually checked (§3.2).
  • domain assumption The RAG knowledge base does not contain write-up-derived solutions for the specific test challenges.
    This is required for a valid evaluation but contradicted by the puffin example (§4.4, Figure 8), where the retrieved payload matches the test challenge.
  • domain assumption The LLM judge (GPT-4-Turbo, cross-checked with Qwen) evaluates open-ended answers without systematic bias.
    Open-ended correctness rates depend on this; only GPT-4-Turbo's answers were cross-checked with a second judge, not all models (§3.5).
  • domain assumption Single-choice questions with deliberately obvious wrong answers measure knowledge rather than recognition of surface cues.
    The question generation prompt requires three options with 'very obvious mistakes' (Appendix C), which may inflate accuracy.
  • domain assumption Prior baseline numbers (NYU CTF) are comparable despite different model versions and environments.
    Table 3 uses results 'obtained directly from the paper by Shao et al.' without re-running in the same environment (§5.1).

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Cite this review

Pith. "Pith review of Measuring and Augmenting Large Language Models for Solving Capture-the-Flag Challenges." pith.science (2026). https://pith.science/paper/U52ITS5N

@misc{pith2026250617644,
  author       = {Pith},
  title        = {Pith review of: Measuring and Augmenting Large Language Models for Solving Capture-the-Flag Challenges},
  year         = {2026},
  howpublished = {\url{https://pith.science/paper/U52ITS5N}},
  note         = {Machine review of arXiv:2506.17644}
}
read the original abstract

Capture-the-Flag (CTF) competitions are crucial for cybersecurity education and training. As large language models (LLMs) evolve, there is increasing interest in their ability to automate CTF challenge solving. For example, DARPA has organized the AIxCC competition since 2023 to advance AI-powered automated offense and defense. However, this demands a combination of multiple abilities, from knowledge to reasoning and further to actions. In this paper, we highlight the importance of technical knowledge in solving CTF problems and deliberately construct a focused benchmark, CTFKnow, with 3,992 questions to measure LLMs' performance in this core aspect. Our study offers a focused and innovative measurement of LLMs' capability in understanding CTF knowledge and applying it to solve CTF challenges. Our key findings reveal that while LLMs possess substantial technical knowledge, they falter in accurately applying this knowledge to specific scenarios and adapting their strategies based on feedback from the CTF environment. Based on insights derived from this measurement study, we propose CTFAgent, a novel LLM-driven framework for advancing CTF problem-solving. CTFAgent introduces two new modules: two-stage Retrieval Augmented Generation (RAG) and interactive Environmental Augmentation, which enhance LLMs' technical knowledge and vulnerability exploitation on CTF, respectively. Our experimental results show that, on two popular CTF datasets, CTFAgent both achieves over 80% performance improvement. Moreover, in the recent picoCTF2024 hosted by CMU, CTFAgent ranked in the top 23.6% of nearly 7,000 participating teams. This reflects the benefit of our measurement study and the potential of our framework in advancing LLMs' capabilities in CTF problem-solving.

Figures

Figures reproduced from arXiv: 2506.17644 by the authors.

Figure 1
Figure 1. The typical progress of solving a CTF challenge. [PITH_FULL_IMAGE:figures/full_fig_p003_1.png] view at source ↗
Figure 2
Figure 2. The standard workflow of RAG. In this paper, we enhance LLMs using a customized version of Retrieval-Augmented Generation (RAG) technology, which incor￾porates knowledge from external databases [49]. As illustrated in [PITH_FULL_IMAGE:figures/full_fig_p003_2.png] view at source ↗
Figure 3
Figure 3. The workflow of building our benchmark. 3.2 CTFKnow Design Motivation. We recognize the necessity for a benchmark that specifically measures LLM capabilities in CTF. Yet, existing bench￾marks, such as Intercode-CTF [89] and NYU CTF Dataset [71], focus on evaluating LLMs’ overall performance in solving CTF challenges. We see this as a limitation, as it is often challenging to disentan￾gle the technical knowledge from… view at source ↗
Figures from the paper (9 more)
Figure 4
Figure 4. Figure 4: A benchmark example, showing extracted technical knowledge along with the single-choice question. The open-ended [PITH_FULL_IMAGE:figures/full_fig_p005_4.png]
Figure 5
Figure 5. Figure 5: LLMs’ correctness rate by difficulty of original chal [PITH_FULL_IMAGE:figures/full_fig_p008_5.png]
Figure 7
Figure 7. Figure 7: The architecture of two-stage RAG system. Firstly, [PITH_FULL_IMAGE:figures/full_fig_p009_7.png]
Figure 8
Figure 8. Figure 8: An example illustrating the working progress of [PITH_FULL_IMAGE:figures/full_fig_p010_8.png]
Figure 9
Figure 9. Figure 9: Cumulative distribution function for the number [PITH_FULL_IMAGE:figures/full_fig_p012_9.png]
Figure 10
Figure 10. Figure 10: Average score distribution of all teams with 1,875 points, CTFAgent, and NYU Framework in picoCTF 2024. and principles of CTFAgent. We can draw the same conclusion from the experimental results of the NYU CTF Dataset. Simultaneously, we observe that the performance of…
Figure 11
Figure 11. Figure 11: Visualization of the 173 clusters obtained by apply￾ing Affinity Propagation to 2,013 CTF technical knowledge points; see the detailed cluster results on our project website. 80 60 40 20 0 20 40 60 t-SNE Dimension 1 40 20 0 20 40 t-SNE Dimension 2 173 Clusters of CTF …
Figure 12
Figure 12. Figure 12: C System Prompts In §3, we designed customized system prompts for the tasks of knowledge extraction, knowledge filtering, question generation (for [PITH_FULL_IMAGE:figures/full_fig_p016_12.png]
Figure 12
Figure 12. Figure 12: Distribution of challenges of various write-up collected in §3 by Year, Type, and Difficulty. Difficulty is determined [PITH_FULL_IMAGE:figures/full_fig_p017_12.png]

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Pith tools

Reviewed August 6, 2026 · model on record in the stance chip above.