MemoryDocDataSet: A Benchmark for Joint Conversational Memory and Long Document Reasoning
Summary
MemoryDocDataSet is a new synthetic benchmark of 50 micro-worlds and 1,000 QA pairs designed to evaluate AI systems on the joint task of conversational memory and long-document reasoning simultaneously. The best baseline (RAG-Both) achieves only 0.358 overall F1, highlighting a significant gap in current systems' ability to unify conversational memory with long-document navigation.
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# MemoryDocDataSet: A Benchmark for Joint Conversational Memory and Long Document Reasoning
Source: [https://arxiv.org/html/2606.04442](https://arxiv.org/html/2606.04442)
Qiyang Xie1Jialun Wu2Xinjie He3Su Liu4 Shuai Xiao4Zhiyuan Lin4Weikai Zhou4 1Northeastern University2Johns Hopkins University 3Columbia University4Independent Researcher
\(June 2026\)
###### Abstract
AI systems increasingly need to combine two demanding capabilities: navigating multi\-session conversation history and performing deep reading comprehension within long documents\. Yet no existing benchmark evaluates both simultaneously\. We introduceMemoryDocDataSet, a synthetic benchmark of 50 micro\-worlds and 1,000 QA pairs in which each instance comprises 3–5 personas, a temporal event graph spanning months of activity, 3–5 real long documents \(20,000–50,000 tokens each sourced from the Caselaw Access Project\), multi\-session conversations grounded on those documents, and 20 question\-answer pairs across five reasoning categories\. The defining feature is theHybridsource tag: questions requiring a system to first navigate conversation history to identify which document is relevant, then extract the answer from within that document\. Hybrid questions account for 75\.1% of the dataset\. Dataset quality is characterised through a prompt\-sensitivity self\-consistency analysis using LLM\-as\-judge, yielding a median Cohen’sκ=0\.634\\kappa=0\.634across all 50 micro\-worlds\. We evaluate six baseline configurations spanning truncated context, long\-context LLMs, retrieval\-augmented generation \(RAG\)\[[1](https://arxiv.org/html/2606.04442#bib.bib1)\], and memory systems\. The best baseline \(RAG\-Both\) achieves 0\.358 overall F1 and 0\.342 on Hybrid\. Document\-only retrieval \(RAG\-Doc\) collapses to 0\.267 on Hybrid despite achieving 0\.453 on Doc\-only questions, demonstrating a clear joint\-retrieval gap that motivates architectures unifying conversational memory with long\-document navigation\. We release the dataset, generation pipeline, and all baseline implementations\.
## 1Introduction
Modern AI assistants operate in settings that demand two capabilities simultaneously\. First, they must maintain coherent memory across long conversations—tracking who said what, when, and how prior context informs the current turn\. Second, they must perform deep reading comprehension within long documents—contracts, reports, filings—that far exceed the size of any conversational exchange\.
These two capabilities have been studied largely in isolation\. Memory benchmarks such as LoCoMo\[[2](https://arxiv.org/html/2606.04442#bib.bib2)\]and LongMemEval\[[3](https://arxiv.org/html/2606.04442#bib.bib3)\]present systems with multi\-session dialogues but attach no long documents; a system that memorizes conversation facts perfectly can score highly\. Long\-document benchmarks such as L\-Eval\[[4](https://arxiv.org/html/2606.04442#bib.bib4)\]and ZeroSCROLLS\[[5](https://arxiv.org/html/2606.04442#bib.bib5)\]present systems with book\-length or report\-length texts but no conversation structure; a system with a large context window can score highly without any notion of memory\.
Neither family of benchmarks measures the combination\. Yet real\-world deployment routinely requires it\. Consider a legal assistant working with a client over several months: it must recall from prior sessions which contract the client is asking about, then navigate 40,000 tokens of that contract to answer a specific question about a penalty clause\. This task is trivial for neither a pure memory system nor a pure long\-context reader\.
We introduceMemoryDocDataSet, a benchmark dataset designed precisely to test this joint capability\. Each instance is amicro\-world—a self\-contained scenario comprising 3–5personaswith defined roles, expertise, and relationships; atemporal event graphof 5–10 time\-stamped events spanning at least six months; 3–5long documentsof 20,000–50,000 tokens each sourced from real public domain legal corpora; fivemulti\-session conversationsgrounded on the event graph in which speakers naturally reference the attached documents; and20 QA pairsper micro\-world spanning five reasoning categories\.
The key novelty is thesource dimension—every QA pair is tagged with whether its answer lies in the conversation history only \(Chat\-only\), in a long document only \(Doc\-only\), or requires bridging both \(Hybrid\)\. Hybrid questions require a system to first use conversation context to identify the relevant document, then read that document deeply to extract the answer\. We require at least 30% of QA pairs per micro\-world to be Hybrid\.
We evaluate six baseline configurations against our benchmark: a truncated\-context base LLM, a long\-context LLM with full context, RAG over conversations only, RAG over documents only, RAG over both, and a memory system baseline\. Results show that all six configurations underperform on Hybrid questions, with RAG over both achieving the highest F1 but still far below expected human performance \(discussed in Section[6\.4](https://arxiv.org/html/2606.04442#S6.SS4)\)\. This gap motivates new systems that tightly integrate conversational memory with long\-document retrieval\.
#### Contributions\.
1. 1\.A benchmark dataset with 50 micro\-worlds, 1,000 QA pairs, and a novel source\-dimension annotation that no existing benchmark provides\.
2. 2\.A fully automated, config\-driven pipeline for generating micro\-worlds at scale using real long documents and LLM\-generated synthetic structure\.
3. 3\.Baseline results across six retrieval and memory configurations, establishing the first systematic comparison on joint conversational memory and long\-document reasoning\.
## 2Related Work
### 2\.1Conversational Memory Benchmarks
Several benchmarks evaluate long\-term conversational memory\. The Beyond Goldfish Memory paper\[[6](https://arxiv.org/html/2606.04442#bib.bib6)\], which introduced the Multi\-Session Chat \(MSC\) dataset, pioneered multi\-session dialogue evaluation but focuses on persona consistency over short \(∼\\sim1K token\) exchanges\. LoCoMo\[[2](https://arxiv.org/html/2606.04442#bib.bib2)\]extends this to longer conversations \(up to 300 turns,∼\\sim9K tokens\) and introduces temporal reasoning questions\. LongMemEval\[[3](https://arxiv.org/html/2606.04442#bib.bib3)\]evaluates LLMs as conversation partners across multiple sessions, with questions probing what was said in prior turns\. MemBench\[[7](https://arxiv.org/html/2606.04442#bib.bib7)\]provides a structured suite of memory operations including storage, retrieval, and update\.
A common limitation across all these benchmarks is the absence of long documents\. The context is entirely conversational; systems that memorize conversation facts well can achieve high scores without any document reading capability\.
### 2\.2Long\-Document and Multi\-hop Benchmarks
A complementary line of work evaluates reading comprehension over long or multi\-document inputs\. L\-Eval\[[4](https://arxiv.org/html/2606.04442#bib.bib4)\]and ZeroSCROLLS\[[5](https://arxiv.org/html/2606.04442#bib.bib5)\]require models to process book\-length or multi\-document texts, but present these as static reading tasks with no conversational component\. HotpotQA\[[8](https://arxiv.org/html/2606.04442#bib.bib8)\]targets multi\-hop reasoning across short Wikipedia passages; it tests inference chains rather than long\-document reading and carries no conversational structure\.
### 2\.3The Gap
Table[1](https://arxiv.org/html/2606.04442#S2.T1)summarizes the key dimensions across related benchmarks\. No existing benchmark combines multi\-session conversations with long documents \(20K\+ tokens\) and requires joint reasoning across both\. MemoryDocDataSet is the first to impose this requirement through the Hybrid source tag\.
Table 1:Comparison of MemoryDocDataSet with related benchmarks\.BenchmarkMulti\-sess\. Conv\.Long Docs \(20K\+\)Joint Reas\.VenueLoCoMo\[[2](https://arxiv.org/html/2606.04442#bib.bib2)\]✓×\\times×\\timesACL 2024LongMemEval\[[3](https://arxiv.org/html/2606.04442#bib.bib3)\]✓×\\times×\\timesICLR 2025MSC\[[6](https://arxiv.org/html/2606.04442#bib.bib6)\]✓×\\times×\\timesACL 2022MemBench\[[7](https://arxiv.org/html/2606.04442#bib.bib7)\]✓×\\times×\\timesACL 2025L\-Eval\[[4](https://arxiv.org/html/2606.04442#bib.bib4)\]×\\times✓×\\timesACL 2024ZeroSCROLLS\[[5](https://arxiv.org/html/2606.04442#bib.bib5)\]×\\times✓×\\timesEMNLP 2023HotpotQA\[[8](https://arxiv.org/html/2606.04442#bib.bib8)\]×\\times×\\times×\\timesEMNLP 2018Ours \(MemoryDocDataSet\)✓✓✓—
### 2\.4Retrieval\-Augmented Generation and Memory Systems
Retrieval\-Augmented Generation \(RAG\)\[[1](https://arxiv.org/html/2606.04442#bib.bib1)\]has emerged as a dominant paradigm for grounding LLM responses in external documents\. However, standard RAG operates over a static document collection indexed at query time, without modeling the temporal structure of conversations or the navigational relationship between conversation context and specific documents\. Memory systems such as Mem0\[[9](https://arxiv.org/html/2606.04442#bib.bib9)\]and Zep\[[10](https://arxiv.org/html/2606.04442#bib.bib10)\]augment LLMs with graph\-based or fact\-based memory stores that track entities and relationships across sessions, but are not designed for deep reading within long documents\. Our benchmark exposes both gaps\.
## 3The MemoryDocDataSet Benchmark
### 3\.1Task Definition
We define the task as follows\. A system is given a micro\-worldMMconsisting of a set of conversation sessionsCCand a set of long documentsDD\. Given a natural language questionqq, the system must produce a free\-text answeraa\. Questions may require evidence fromCCalone, fromDDalone, or from both—and the system receives no signal at test time about which source is required\. Evaluation is performed using Exact Match \(EM\) and token\-level F1 against gold answers, with a separate abstention accuracy metric for adversarial questions\.
This formulation is intentionally representation\-agnostic: the system may representCCandDDas a flat context, a vector index, a knowledge graph, or any other structure\. The benchmark does not prescribe a retrieval or memory architecture\.
### 3\.2Micro\-World Structure
Figure 1:Structure of a MemoryDocDataSet micro\-world\. Each micro\-world comprises personas, a temporal event graph, long documents, multi\-session conversations, and QA pairs annotated with source tags \(Chat\-only, Doc\-only, Hybrid\)\.The fundamental unit of the dataset is themicro\-world—a self\-contained scenario that provides all context needed to answer its associated questions\. Figure[1](https://arxiv.org/html/2606.04442#S3.F1)illustrates the structure\. Formally, a micro\-world is a tupleM=\(P,G,D,C,Q\)M=\(P,G,D,C,Q\)\.
#### PP\(Personas\)\.
PPis a set ofpersonas, each described by a name, professional role, domain expertise, communication style, and a set of directed relationships to other personas \(e\.g\.,reports to,collaborates with\)\. Each micro\-world contains 3–5 personas\.
#### GG\(Event Graph\)\.
GGis atemporal event graph—a directed acyclic graph \(DAG\) over a set of time\-stamped events\. Each evente∈Ge\\in Ghas a timestamp, a natural language description, a subset of personas involved, and a subset of documents referenced\. Events span a minimum of six months of simulated activity\. The DAG structure encodes causal dependencies between events\.
#### DD\(Documents\)\.
DDis a set oflong documents, each containing 20,000–50,000 tokens of real legal text sourced from the Caselaw Access Project\[[11](https://arxiv.org/html/2606.04442#bib.bib11)\]\. Each micro\-world contains 3–5 documents\. Documents are shared across personas and events within a micro\-world, grounding the scenario in a consistent body of written evidence\.
#### CC\(Conversations\)\.
CCis a set ofconversation sessions\. Each sessions∈Cs\\in Cis anchored to a specific evente∈Ge\\in G, involves a subset of personas fromPP, and consists of a sequence of utterances\. Sessions are ordered chronologically and collectively span the timeline ofGG\. At least 40% of sessions explicitly reference one or more documents inDD, establishing the navigational relationship between conversation context and document content that defines Hybrid questions\.
#### QQ\(QA Pairs\)\.
QQis a set ofQA pairs\. Eachq∈Qq\\in Qconsists of a natural language question, a gold free\-text answer, a category label \(Section[3\.3](https://arxiv.org/html/2606.04442#S3.SS3)\), a source tag \(Section[3\.4](https://arxiv.org/html/2606.04442#S3.SS4)\), and one or more evidence references pointing to the specific utterance or document passage that supports the answer\. Each micro\-world contains 20 QA pairs\.
### 3\.3Question Categories
We adopt five question categories following the taxonomy established in LoCoMo\[[2](https://arxiv.org/html/2606.04442#bib.bib2)\], which has become the standard for memory benchmark evaluation\. Table[2](https://arxiv.org/html/2606.04442#S3.T2)defines each category with an example drawn from the legal domain\.
Table 2:QA categories, definitions, and examples\.These five categories are not mutually exclusive in general, but in our annotation each QA pair is assigned exactly one primary category\. For Adversarial questions, we additionally record the adversarial type \(false premiseorunanswerable\) and evaluate systems separately on abstention accuracy—the rate at which a system correctly declines to answer rather than producing a hallucinated response\.
### 3\.4The Source Dimension
The defining contribution of MemoryDocDataSet is thesource dimension: an orthogonal annotation on every QA pair that identifies which information sources are required to answer the question\. Each QA pair carries exactly one of three mutually exclusive source tags\.
#### Chat\-only\.
The gold answer is fully derivable from the conversation sessionsCC; no document inDDneeds to be read\. This tag tests standard conversational memory and is comparable to questions in LoCoMo\[[2](https://arxiv.org/html/2606.04442#bib.bib2)\]and LongMemEval\[[3](https://arxiv.org/html/2606.04442#bib.bib3)\]\.
#### Doc\-only\.
The gold answer requires reading one or more documents inDD; the conversation sessions provide no additional signal\. This tag tests long\-document comprehension and is comparable to questions in L\-Eval\[[4](https://arxiv.org/html/2606.04442#bib.bib4)\]and ZeroSCROLLS\[[5](https://arxiv.org/html/2606.04442#bib.bib5)\]\.
#### Hybrid\.
Answering requires two steps: first, the system must use the conversation sessionsCCto identifywhichdocument inDDis relevant—typically because a persona references a specific document during a session; second, it must read that document to extract the answer\. Neither step alone is sufficient\. This tag has no equivalent in any prior benchmark\.
We enforce that at least 30% of QA pairs per micro\-world carry the Hybrid tag\. Critically, every Hybrid QA pair is verified to satisfy two structural conditions: \(1\) at least one session inCCcontains an explicit reference to the document required to answerqq, and \(2\) the gold answer cannot be derived fromCCalone, requiring the system to actually read the referenced document\.
### 3\.5Dataset Statistics
MemoryDocDataSet v1\.0 comprises50 micro\-worldsin the legal domain \(US caselaw sourced from the Caselaw Access Project\), split 70/14/16 into train, validation, and test sets at the micro\-world level \(35/7/8 worlds respectively; the slight asymmetry reflects integer division of 50 whole micro\-worlds\)\. Table[3](https://arxiv.org/html/2606.04442#S3.T3)summarizes the measured structural properties of the released dataset, and Table[4](https://arxiv.org/html/2606.04442#S3.T4)shows the QA pair distribution\.
Table 3:MemoryDocDataSet v1\.0 structural properties\. Documents are sourced from the Caselaw Access Project\[[11](https://arxiv.org/html/2606.04442#bib.bib11)\]\.Table 4:QA pair distribution by category, source tag, and difficulty\.DimensionLabelCount%CategorySingle\-hop20020\.0%Multi\-hop20020\.0%Temporal20020\.0%Know\. Update20020\.0%Adversarial20020\.0%Source tagHybrid75175\.1%Chat\-only13613\.6%Doc\-only11311\.3%DifficultyMedium38938\.9%Hard32132\.1%Easy29029\.0%QA pairs are distributed uniformly across the five question categories \(20% each\) by construction\. The Hybrid source tag accounts for 75\.1% of all pairs, substantially exceeding the 30% design floor, reflecting the fact that most questions in a scenario grounded on real documents naturally require bridging conversation and document evidence\. The test split \(160 pairs, 8 worlds\) is the evaluation set used in all baseline experiments reported in Section[5](https://arxiv.org/html/2606.04442#S5)\.
### 3\.6Quality Analysis
We conduct a full\-coverage automated quality analysis using an LLM\-as\-judge protocol applied to all 50 micro\-worlds\. Two judge instances are instantiated from the same model \(Claude Sonnet 4\.6\) with contrasting system prompts: astrict reviewerinstructed to flag any QA pair whose gold answer is not unambiguously supported by the cited evidence, and alenient reviewerinstructed to accept answers that are consistent with the evidence under any reasonable reading\. Each judge independently scores every QA pair in a world as correct or incorrect, producing two binary label vectors per world over which Cohen’sκ\\kappais computed\.
This design measuresprompt\-sensitivity self\-consistency: the degree to which the pipeline’s quality signal is stable across different interpretive stances toward the same evidence\. It is not equivalent to human inter\-annotator agreement—the two judges share a model family with the generation pipeline, which may introduce leniency bias—but it provides a reproducible, scalable proxy for labeling consistency\.
Across all 50 micro\-worlds, the median prompt\-sensitivityκ\\kappais0\.634\(mean 0\.619, range 0\.000–1\.000\)\. 22 worlds \(44%\) achieveκ≥0\.70\\kappa\\geq 0\.70\(substantial agreement\), 29 worlds \(58%\) achieveκ≥0\.60\\kappa\\geq 0\.60, and 41 worlds \(82%\) achieveκ≥0\.40\\kappa\\geq 0\.40\. All 50 worlds are retained in the released dataset; the per\-worldκ\\kappavalues are published alongside the data to allow downstream users to apply their own quality filters\. Worlds with lowκ\\kappapredominantly arise from a systematic base\-rate gap between the two prompts—the strict judge accepts roughly 40% of QA pairs per world while the lenient judge accepts roughly 55%—rather than from disagreement about specific pairs\. This base\-rate effect mathematically caps achievableκ\\kappafor worlds where the gap is large, independent of actual QA correctness\. We discuss this limitation further in Section[6\.4](https://arxiv.org/html/2606.04442#S6.SS4)\.
## 4Collection Pipeline
MemoryDocDataSet is generated by an automated seven\-stage pipeline that combines real document sourcing with LLM\-driven synthetic structure generation\. The pipeline is fully reproducible, config\-driven, and supports checkpoint/resume to handle long runs\.
### 4\.1Overview
The seven stages are: \(1\) Document Collection, \(2\) Persona & Event Graph Generation, \(3\) Conversation Generation, \(4\) QA Generation, \(5\) Quality Verification, \(6\) Dataset Packaging, and \(7\) Baseline Evaluation\. All generation calls in Stages 1–5 use Claude Sonnet 4\.6 via the Anthropic API\. All LLM calls are routed through a unified client supporting multiple providers \(Groq, Ollama, Anthropic, OpenAI\), making the pipeline provider\-agnostic\. Figure[2](https://arxiv.org/html/2606.04442#S4.F2)provides an overview of the full pipeline with per\-stage outputs\.
Figure 2:Seven\-stage generation and evaluation pipeline\. Each stage is independently reproducible; the pipeline supports checkpoint/resume for long runs\.
### 4\.2Stage 1: Document Collection
Long documents are sourced from theCaselaw Access Project\[[11](https://arxiv.org/html/2606.04442#bib.bib11)\], a Harvard Law School initiative that has digitized 6\.9 million US court opinions spanning all jurisdictions from the founding era to approximately 2020\. Individual case opinions typically range from 5,000 to 20,000 characters\. We bundle full reporter volumes into single documents, reaching our 20,000–50,000 token target\. Documents are validated using thecl100k\_basetokenizer and must carry a permissive license\. The current corpus covers 10 US jurisdictions with planned expansion to all 50 states\.
### 4\.3Stage 2: Persona and Event Graph Generation
For each micro\-world, an LLM generates a set of 3–5 personas and a temporal event graph grounded on the collected documents\. The event graph is a DAG of 5–10 time\-stamped events, each referencing one or more personas and one or more documents, spanning a minimum of six months of simulated activity\. Event graphs are validated for structural correctness \(no cycles, all referenced entities exist\) before advancing\.
### 4\.4Stage 3: Conversation Generation
An LLM generates 5 dialogue sessions for each micro\-world, grounded on the event graph\. Each session is anchored to a specific event and involves a subset of the micro\-world’s personas\. A grounding ratio of at least 40% of sessions must reference at least one document, enforcing that conversations are not purely self\-contained\.
### 4\.5Stage 4: QA Generation
QA pairs are generated across five categories adapted from the LoCoMo taxonomy\[[2](https://arxiv.org/html/2606.04442#bib.bib2)\]: single\-hop, multi\-hop, temporal, knowledge update, and adversarial\. Each QA pair is additionally annotated with a source tag; at least 30% of QA pairs per micro\-world must be Hybrid\. Gold answers include evidence references pointing to the specific conversation turn or document passage that supports the answer\.
### 4\.6Stage 5: Quality Verification
All 50 micro\-worlds are assessed using the LLM\-as\-judge protocol described in Section[3\.6](https://arxiv.org/html/2606.04442#S3.SS6)\. The per\-worldκ\\kappavalues are recorded and published with the dataset release\. All worlds are retained regardless ofκ\\kappavalue \(agreement\_threshold: 0\.0\);κ\\kappais reported as a prompt\-sensitivity quality characterisation rather than a hard filter \(see Section[3\.6](https://arxiv.org/html/2606.04442#S3.SS6)for rationale\)\.
### 4\.7Stage 6: Dataset Packaging
Verified micro\-worlds are split 70/14/16 into train, validation, and test sets at the micro\-world level\. Splitting is performed with document isolation: no document appears in more than one split, preventing leakage\. The dataset is serialized to JSON with accompanying statistics and a Datasheets for Datasets\[[12](https://arxiv.org/html/2606.04442#bib.bib12)\]documentation file\.
## 5Baseline Experiments
We evaluate six baseline configurations that span the design space of current approaches to conversational memory and long\-document retrieval\. These baselines are intended to establish lower and upper bounds on the benchmark and to characterize where each class of approach succeeds and fails—not to achieve state\-of\-the\-art performance\.
### 5\.1Experimental Setup
All baselines useClaude Sonnet 4\.5for answer generation\. The dataset itself was generated with Claude Sonnet 4\.6, keeping generation and evaluation models distinct to avoid self\-evaluation bias\. Documents are chunked into 512\-token windows with 64\-token overlap\. Chunk embeddings are computed with theall\-MiniLM\-L6\-v2sentence encoder\[[13](https://arxiv.org/html/2606.04442#bib.bib13)\]and indexed in a persistent ChromaDB\[[14](https://arxiv.org/html/2606.04442#bib.bib14)\]vector store\. Retrieval uses cosine similarity withk=10k\{=\}10chunks; this value was not tuned on the validation split and hyperparameter sensitivity is left to future work\. All experiments are conducted on the test split only \(160 QA pairs, 8 micro\-worlds\); the train and validation splits are reserved for system development\.
### 5\.2Baselines
We define six baseline configurations, summarized in Table[5](https://arxiv.org/html/2606.04442#S5.T5)\.
Table 5:Baseline configurations\.#### Base LLM
concatenates all conversation sessions and document text for the relevant micro\-world and truncates to a 4,096\-token context window\. This serves as a lower bound, since it can only use whatever fits in the window\.
#### Long\-Context LLM
provides the full concatenation of conversation sessions and document text up to a 60,000\-token context limit\. It tests whether a long\-context model can solve the benchmark purely through extended attention\.
#### RAG\-Conv
indexes only conversation utterances\. At inference time, the top\-kkutterance chunks most similar to the question are retrieved\. This configuration is directly comparable to retrieval\-augmented approaches used in existing memory benchmarks\[[2](https://arxiv.org/html/2606.04442#bib.bib2),[3](https://arxiv.org/html/2606.04442#bib.bib3)\], and has no access to document content\.
#### RAG\-Doc
indexes only document chunks\. This is the natural RAG approach for long\-document QA benchmarks\[[4](https://arxiv.org/html/2606.04442#bib.bib4),[5](https://arxiv.org/html/2606.04442#bib.bib5)\]and serves as a strong Doc\-only baseline\. It has no access to conversation history\.
#### RAG\-Both
indexes both conversation utterances and document chunks into a unified vector store and retrieves the top\-kkchunks across both modalities, ranked jointly by similarity score\. This is the strongest retrieval baseline\.
#### Memory System
implements a fact\-extraction memory layer on top of ChromaDB\[[14](https://arxiv.org/html/2606.04442#bib.bib14)\]\. For each conversation session, an LLM prompt extracts up to 10 key facts as a structured list; these facts are embedded and stored in a dedicated vector collection\. At query time, the top\-kkmost similar facts are retrieved as context\. Unlike the RAG baselines, which operate on raw text chunks, the Memory System stores semantic abstractions of conversations\. Importantly, conversation sessions frequently reference and paraphrase document content, so the extracted facts can capture document\-derived information indirectly—explaining the system’s competitive Doc\-only score despite having no direct access to document chunks\.
### 5\.3Evaluation Metrics
#### Exact Match \(EM\)
A prediction is correct if, after normalization \(lowercasing, removing articles and punctuation\), it exactly matches the gold answer string\.
#### Token\-level F1
The harmonic mean of precision and recall computed over the bag of tokens in the predicted and gold answers, after the same normalization\.
#### Abstention Accuracy
For Adversarial questions only, we evaluate whether the system correctly abstains rather than producing a hallucinated answer\. A system is instructed to respond with the special tokenABSTAINwhen it cannot answer from the provided context\. This metric is reported separately and not included in overall EM or F1\.
Token\-level F1 and Abstention Accuracy are reported overall and broken down along two dimensions: \(1\) question category and \(2\) source tag\. Exact Match is omitted from the main tables as free\-text answers rarely produce exact string matches; F1 is the primary metric throughout\. The per\-source\-tag F1 breakdown is the primary diagnostic for measuring the joint reasoning gap\.
### 5\.4Results
Tables[6](https://arxiv.org/html/2606.04442#S5.T6)and[7](https://arxiv.org/html/2606.04442#S5.T7)report F1 results on the test split\.
Table 6:Token\-level F1 per baseline by source tag \(test split,n=160n\{=\}160\)\. Abstention Accuracy \(AbstAcc\) is reported separately for Adversarial questions \(n=32n\{=\}32\)\. Bold indicates the highest value in each column\. Test\-split counts for Doc\-only \(n=23n\{=\}23\) and Chat\-only \(n=16n\{=\}16\) are small; per\-tag differences should be interpreted with appropriate caution regarding statistical power\.Table 7:Token\-level F1 per baseline by question category \(test split,n=160n\{=\}160, 32 per category\)\.The most striking pattern in Table[6](https://arxiv.org/html/2606.04442#S5.T6)is theasymmetry of specialization\. RAG\-Doc achieves the second\-highest F1 on Doc\-only questions \(0\.453\) but thelowestoverall score \(0\.296\) due to near\-collapse on Hybrid questions \(0\.267\)\. This directly demonstrates that document retrieval without conversational navigation is insufficient for joint reasoning\. RAG\-Both recovers this gap, improving Hybrid F1 from 0\.267 to 0\.342 by incorporating conversation retrieval alongside document retrieval\.
Long\-Context LLM ranks fourth overall \(0\.323\) despite receiving the full 60,000\-token context window\. Its comparatively low abstention accuracy \(0\.844 vs\. 0\.938–1\.000 for retrieval baselines\) indicates that attending over very long contexts increases the tendency to fabricate answers for unanswerable questions\. The Memory System \(0\.325 overall\) is competitive with the long\-context approach, particularly on Doc\-only questions \(0\.459\), where its fact\-extraction layer distils document\-referenced facts from conversations into easily retrievable form\.
In Table[7](https://arxiv.org/html/2606.04442#S5.T7), all baselines show relatively uniform F1 across categories \(range 0\.267–0\.431\), with the exception of RAG\-Doc which degrades sharply on Temporal \(0\.220\) and Knowledge Update \(0\.233\) questions—categories requiring tracking evolving state across sessions, information unavailable to document\-only retrieval\. Multi\-hop questions are consistently the weakest category for retrieval baselines \(RAG\-Both: 0\.298\), suggesting that chaining evidence across two or more retrieval steps remains an open challenge\.
## 6Discussion
### 6\.1Do Hybrid Questions Expose a Genuine Joint\-Retrieval Gap?
The answer is partially yes, but with important nuance\. For baselines that specialize on one modality, Hybrid is clearly the hardest source tag: RAG\-Doc scores 0\.267 on Hybrid versus 0\.453 on Doc\-only, and Memory System scores 0\.302 on Hybrid versus 0\.459 on Doc\-only\. The pattern is consistent—a system that lacks access to one modality is penalized precisely on the questions that require it\.
However, the gap is less pronounced for baselines that have access to all context\. Long\-Context LLM actually scoreshigheston Hybrid \(0\.330\) among the three source tags, outperforming its own Doc\-only score \(0\.318\), likely because Hybrid questions tend to have richer evidence in the conversation turns and because the question text echoes conversational phrasing\. The specialization asymmetry—strong on one source tag, weak on the complementary tag—is the clearest signal that the benchmark is measuring something real\.
### 6\.2Does RAG\-Both Improve Over Specialised Baselines on Hybrid?
RAG\-Both \(Hybrid F1=0\.342\) substantially outperforms RAG\-Doc \(0\.267\) on Hybrid questions, confirming that incorporating conversation retrieval recovers most of the gap caused by document\-only indexing\. However, RAG\-Both does not substantially outperform RAG\-Conv \(0\.348\) on Hybrid questions\. This is a striking finding: on Hybrid questions, conversation\-side retrieval appears to carry most of the weight\. The likely explanation is that Hybrid question text tends to echo conversation language \(persona names, event references\) more closely than it echoes specific document terminology, making conversation chunks more similar to queries in embedding space\.
This result suggests that the joint retrieval challenge in Hybrid questions is not symmetric: the hard part is identifyingwhich documenta conversation references \(a navigation problem\), not retrieving passages from that document once it is identified\. No baseline we evaluate implements this two\-stage strategy\.
### 6\.3Does Long\-Context LLM Outperform Base LLM?
Despite a 15×\\timescontext size increase \(4,096→\\to60,000 tokens\), Long\-Context LLM achieves only a marginal overall improvement over Base LLM \(0\.323 vs\. 0\.317 F1\)\. On Doc\-only questions, Long\-Context LLM is actuallyworsethan Base LLM \(0\.318 vs\. 0\.339\), and its abstention accuracy is the lowest of all baselines \(0\.844 vs\. 0\.938 for Base LLM\)\. This pattern is consistent with the “lost in the middle” failure mode documented for long\-context transformers\[[15](https://arxiv.org/html/2606.04442#bib.bib15)\], in which relevant content embedded deep within a long context is systematically underweighted by attention\. The practical implication is that expanding the context window is not a substitute for structured retrieval\. Systems with access to the full context but no retrieval mechanism do not substantially outperform systems that see only 4,096 tokens of it—while simultaneously becoming less reliable on adversarial questions\. Taken together, the results across all six baselines suggest that neither context length nor fact\-based memory substitutes for structured joint retrieval—the core design challenge this benchmark is intended to expose\.
### 6\.4Human\-System Gap
A formal human performance upper bound has not been measured in this work and remains an important direction for future evaluation\. Recruiting domain\-knowledgeable annotators for caselaw material, ensuring sufficient annotation time for long\-document comprehension, and controlling for individual variance all require infrastructure beyond the current scope\.
We anticipate the human\-system gap to be substantial, particularly on Hybrid questions\. As a partial quality signal, our LLM\-as\-judge verification \(Section[3\.6](https://arxiv.org/html/2606.04442#S3.SS6)\) found that the lenient judge accepted 67% of QA pairs overall, with higher acceptance on Doc\-only \(96%\) and Chat\-only \(61%\) questions than on Hybrid \(44%\)\. The lower Hybrid acceptance rate is consistent with the difficulty observed in baseline F1 scores\. Future work reporting human F1 on a sample of≥\\geq50 test questions would anchor the benchmark’s difficulty and provide a concrete target for system improvement\.
### 6\.5Implications for System Design
The results collectively point to a specific architectural gap\. No existing approach—long\-context attention, retrieval over one modality, retrieval over both, or fact\-based memory—implements the two\-step process that Hybrid questions require: \(1\) use conversation context to identifywhichdocument is relevant, and \(2\) retrieve specifically from that document\. RAG\-Both comes closest but does so with a flat similarity ranking that cannot enforce the navigational dependency between step 1 and step 2\.
A system that could close the Hybrid gap would need at minimum: \(a\) a representation of which conversation sessions reference which documents \(a citation graph\), and \(b\) a retrieval strategy that conditions document\-chunk retrieval on the output of conversation\-level retrieval\. Memory systems designed around entity and relationship graphs \(e\.g\., Mem0\[[9](https://arxiv.org/html/2606.04442#bib.bib9)\], Zep\[[10](https://arxiv.org/html/2606.04442#bib.bib10)\]\) could in principle encode document references as graph edges, but neither system in its current form is designed for this use case\. MemoryDocDataSet makes the gap measurable and provides the scaffolding for evaluating future approaches that attempt to close it\.
## Limitations
Domain scope\.The current document corpus is drawn entirely from US court opinions sourced from the Caselaw Access Project\[[11](https://arxiv.org/html/2606.04442#bib.bib11)\]\. While legal text is a natural fit for the benchmark, it introduces domain bias\. We plan to expand to additional document types and domains in future releases\.
LLM\-generated conversation quality\.Conversation sessions are generated by a language model conditioned on the event graph and document set\. LLM\-generated dialogues may not capture the full range of natural language phenomena found in real human conversations—including implicit references, pragmatic inferences, code\-switching, and repair sequences\.
Automated QA generation\.QA pairs and gold answers are produced by an LLM and validated through structural checks\. Automated generation cannot guarantee that every gold answer is uniquely correct, that distractors in Adversarial questions are sufficiently realistic, or that Knowledge Update questions capture all intermediate states\.
LLM\-as\-judge verification limitations\.Quality verification is performed by two LLM judge instances from the same model family as the generation pipeline, introducing potential self\-leniency bias\. Additionally, the prompt\-sensitivityκ\\kappawe measure reflects base\-rate differences between strict and lenient prompts as much as genuine label disagreement\.
English only\.The pipeline and document corpus are currently English\-only\.
Synthetic scenario realism\.Micro\-world personas, event graphs, and conversation sessions are synthetically generated\. The temporal event graphs enforce a clean DAG structure, which may be more regular than the overlapping, ambiguous timelines found in real cases\.
Fixed Hybrid threshold\.The 30% Hybrid question floor is a dataset design parameter chosen to ensure reliable per\-source\-tag metrics\. It is not empirically derived from a study of real\-world task distributions\.
## 7Conclusion
We introduced MemoryDocDataSet to close a gap that existing benchmarks leave open: no prior work evaluates AI systems on the joint task of navigating multi\-session conversation historyandperforming deep reading within long documents simultaneously\. The Hybrid source tag formalizes this requirement—questions that are unanswerable without first using conversation context to identify the relevant document, then reading that document to extract the answer\.
Our baseline experiments reveal a clearspecialization asymmetrywith direct implications for system design\. RAG\-Doc, the natural approach for long\-document QA, collapses to 0\.267 F1 on Hybrid despite achieving 0\.453 on Doc\-only—a 41% relative drop caused by the structural inability of document\-only retrieval to resolve which document a conversation is referring to\. RAG\-Both closes much of this gap \(Hybrid F1=0\.342\) but the remaining shortfall points to the core open problem: no existing baseline implements the two\-step navigational strategy that Hybrid questions require\. A system that first uses conversation retrieval to identify the relevant document, then applies targeted retrieval within that specific document, would be architecturally suited to this task—and no current approach does so\.
The practical implication is that the next generation of AI assistants will need to couple conversational memory with long\-document navigation at the architectural level, not just at the context\-window level\. MemoryDocDataSet makes this gap measurable, reproducible, and quantifiable for the first time\. We release the dataset, generation pipeline, and all baseline implementations to support this line of research\.
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## Appendix
## Appendix APipeline Stage Details
#### Stage 1 — Document Collection\.
Raw opinions are downloaded from the Caselaw Access Project bulk export and processed into long document objects\. Each document is tokenized withcl100k\_baseand filtered to 20,000–50,000 tokens\. Documents are deduped by case ID and split into per\-state shards to support reproducible batched runs\.
#### Stage 2 — Persona & Event Graph Generation\.
For each micro\-world the pipeline selects 3–5 documents at random \(without replacement\), infers a domain label from their content, and calls the persona and event\-graph generators in sequence\. Persona count is sampled frompersonas\_per\_world\(default 3–5\)\. Event count is sampled fromevents\_per\_graph\(default 5–10\)\. The event graph is validated as a DAG before acceptance; malformed graphs are retried up to three times\.
#### Stage 3 — Conversation Generation\.
Sessions are generated one per event in topological order of the event graph, so that each session can reference prior\-session context\. A grounding flag controls whether a session must include at least one document citation \(applied togrounding\_ratio\_threshold×\\timessessions\)\. Each session is generated independently, making the stage trivially parallelisable\.
#### Stage 4 — QA Generation\.
Five category\-specific prompts are called per micro\-world\. A post\-generation filter enforces at leastmin\_qa\_per\_categorypairs per category and at leastdoc\_navigation\_ratiopairs withrequires\_doc\_navigation=true\. Pairs failing structural validation are discarded; the stage retries if minimum counts are not met\.
#### Stage 5 — Quality Verification\.
Two LLM judge instances \(strict and lenient system prompts, same base model\) evaluate every micro\-world in parallel\. Each judge returns per\-QA correctness labels \(qa\_answer\_correctness\) and per\-world Likert quality scores \(persona consistency, temporal coherence, document grounding accuracy, 1–5\)\. Cohen’sκ\\kappais computed over theqa\_answer\_correctnesslabels\. All micro\-worlds are retained regardless ofκ\\kappavalue \(agreement\_threshold: 0\.0\);κ\\kappais reported as a prompt\-sensitivity quality characterisation rather than a hard filter \(see Section[3\.6](https://arxiv.org/html/2606.04442#S3.SS6)for rationale\)\.
#### Stage 6 — Dataset Packaging\.
Verified micro\-worlds are shuffled \(seed fixed torandom\_seed\) and split 70/14/16 into train, validation, and test sets at the micro\-world level\. No QA pair from one split shares a micro\-world with another split\. Document\-level leakage is also prevented: a document assigned to a micro\-world in the test split does not appear in any train or validation micro\-world\.
#### Stage 7 — Baseline Evaluation\.
Each baseline system is given the question text and the access mode appropriate to its design\. Predictions are scored against gold answers using token\-level F1 and exact match after lowercasing, article removal, and punctuation stripping\. Abstention accuracy is computed separately for Adversarial questions using a reservedABSTAINtoken\.
## Appendix BPrompt Templates
All LLM calls use a two\-part message: a system prompt setting the generator’s role and a user prompt containing the structured input and output schema\. Templates are reproduced verbatim below; slot names in\{braces\}are filled at runtime\.
### B\.1Persona Generation
System promptYou are a creative writer specializing in generating realistic professional personas for synthetic dataset generation\. You produce well\-structured JSON output that strictly follows the requested schema\.
User promptGenerate\{count\}unique professional personas for a micro\-world in the “\{domain\}” domain\. Each persona must have: a unique full name; a professional role relevant to the domain; an expertise domain; a communication style; relationships to other personas\. Return a JSON array where each element has:name,role,expertise\_domain,communication\_style,relationships\. Document summaries for context:\{document\_summaries\}\. Return ONLY valid JSON, no markdown fences or extra text\.
### B\.2Event Graph Generation
System promptYou are an expert at creating realistic temporal event sequences for professional scenarios\. You produce well\-structured JSON output that strictly follows the requested schema\. Events must form a valid directed acyclic graph \(DAG\) with no cycles\.
User promptGenerate a temporal event graph with\{event\_count\}events for a “\{domain\}” micro\-world\. Events must span at least\{time\_span\_months\}months, form a valid DAG, reference at least one persona and one document each, and ensure every document is referenced by at least one event\. Return a JSON object with:time\_range\_start,time\_range\_end, and aneventsarray\. Each event has:event\_id,timestamp\(ISO 8601\),description,persona\_ids,document\_ids,depends\_on\. Return ONLY valid JSON, no markdown fences or extra text\.
### B\.3Conversation Session Generation
System promptYou are an expert dialogue writer who creates realistic multi\-party professional conversations\. You produce well\-structured JSON output that strictly follows the requested schema\. Conversations must be grounded in the provided event context and reference documents when appropriate\.
User promptGenerate a realistic conversation session for the following event in a “\{domain\}” scenario\. Event:\{event\_description\}at\{event\_timestamp\}\. Participating personas:\{personas\_json\}\. Documents available for reference:\{documents\_json\}\. Prior conversation context:\{prior\_context\}\. Instructions: generate natural dialogue; respect each persona’s communication style; include temporal markers;\{grounding\_instruction\}; aim for\{target\_utterances\}utterances\. Return a JSON object with anutterancesarray andreferenced\_document\_ids\. Return ONLY valid JSON\.
### B\.4QA Generation
All five category prompts share the same system prompt:
System prompt \(shared across all five categories\)You are an expert benchmark dataset creator who generates high\-quality question\-answer pairs for evaluating AI systems on joint conversational memory and long document reasoning\. You produce well\-structured JSON output that strictly follows the requested schema\.
Category\-specific core instructions are summarized in Table[8](https://arxiv.org/html/2606.04442#A2.T8)\. All category prompts request the same output schema per QA pair:question,gold\_answer,evidence\_references\(withsource\_type,source\_id,passage\_span\),difficulty,requires\_doc\_navigation\.
Table 8:QA generation category\-specific instructions\.
### B\.5LLM\-as\-Judge \(Quality Verification\)
Two instances of the same model are run with contrasting system prompts and an identical user prompt body\.
Strict system promptYou are a strict quality reviewer for a benchmark dataset of QA pairs grounded in conversations and long documents\. Apply skeptical scrutiny: if a QA pair’s gold answer is not unambiguously supported by the cited evidence, mark it incorrect\. If a question’s category label is debatable, mark it inaccurate\. Err on the side of flagging\. Output a single JSON object matching the requested schema\. Do not add commentary outside the JSON\.
Lenient system promptYou are a charitable quality reviewer for a benchmark dataset of QA pairs grounded in conversations and long documents\. Apply reasonable interpretation: if the gold answer is consistent with the cited evidence under any reasonable reading, mark it correct\. Only flag clear errors or unsupported claims\. Output a single JSON object matching the requested schema\. Do not add commentary outside the JSON\.
#### User prompt \(shared\)\.
A compact context is rendered per micro\-world containing the list of personas, the full conversation sessions, and each QA pair with its cited evidence excerpts inlined\. The judge returns a JSON object withpersona\_consistency\(1–5\),temporal\_coherence\(1–5\),document\_grounding\_accuracy\(1–5\),qa\_answer\_correctness\(map of QA ID→\\tobool\),qa\_category\_accuracy\(map of QA ID→\\tobool\),flagged\_qa\_ids, andnotes\.
## Appendix CDataset Example
Below is an illustrative excerpt from one micro\-world in the caselaw domain \(all names and case references are from authentic Caselaw Access Project documents\)\.
Personas \(excerpt\)•Margaret Chen— Senior Partner; contract law; “formal and precise”•David Rodriguez— Associate Attorney; litigation; “analytical and thorough”•Sarah Kim— Legal Researcher; case law research; “methodical and detail\-oriented”
Event graph \(excerpt, 3 of 7 events\)•evt\-1\(2024\-01\-10\): Initial client consultation on breach of contract; involves Chen, Rodriguez; references Case A\.•evt\-3\(2024\-02\-14\): Discovery of precedent contradicting client position; involves Kim; references Case B\.•evt\-5\(2024\-03\-22\): Strategy revision meeting; involves all three personas; references Cases A and B\.
QA example — Single\-hopQ:Which attorney conducted the initial client consultation on the breach of contract claim? A:Margaret Chen and David Rodriguez\. Source:evt\-1conversation session\.
QA example — Hybrid \(doc navigation required\)Q:What specific contractual clause did the precedent case identified by Kim in February establish as unenforceable? A:\[answer drawn from Case B document after identifying it viaevt\-3conversation\] Source:evt\-3conversation session→\\toCase B document\.
QA example — Knowledge UpdateQ:What was the legal team’s recommended strategy for the breach of contract case as of March 2024? A:\[revised strategy fromevt\-5, superseding the initial strategy fromevt\-1\] Source:evt\-5conversation session;evt\-1\(superseded\)\.Similar Articles
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