PRAGMA: Evaluating Personalized Guidance with Memory Alignment in Lifelong Conversations

AuthorsHyojeong Yu, Hyukhun Koh, Minsung Kim et al.

arXiv 20262026

TL;DR

PRAGMA uses a controlled conversational history pipeline and a four-way query taxonomy to show that even oracle evidence access leaves grounding below 86.00 on trajectory guidance.

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THE PROBLEM

Personalized assistants fail to ground guidance in long histories

PRAGMA shows that No-Context responses have near-zero grounding, for example 0.00 grounding on Trajectory-Align queries.

In long-term personalized guidance, systems ignore distributed evidence, causing misaligned recommendations and failures on corrective reasoning over evolving user trajectories.

HOW IT WORKS

PRAGMA benchmark design for memory-grounded guidance

PRAGMA builds on a User Schema, annotated Evidence, long Sessions, and diverse Queries to stress-test memory-grounded guidance.

Think of PRAGMA as a carefully scripted life log plus a card catalog: events and trajectories are stored, indexed, and then probed with tricky guidance questions.

This design lets PRAGMA expose failures that a plain context window cannot, especially when evidence is temporally scattered and user assumptions are memory-misaligned.

DIAGRAM

PRAGMA query taxonomy and memory dynamics

This diagram shows how PRAGMA organizes guidance queries by memory dynamics and alignment with conversational evidence.

DIAGRAM

PRAGMA benchmark construction pipeline

This diagram shows how PRAGMA builds synthetic users, generates conversations, and annotates evidence for evaluation.

PROCESS

How PRAGMA Handles a Personalized Guidance Query

  1. 01

    Query Design

    PRAGMA first classifies the user request into Event-Align, Event-Correct, Traj-Align, or Traj-Correct using the Query Taxonomy to control memory dynamics.

  2. 02

    Conversation History Construction

    PRAGMA expands Evidence Events and Trajectory states into Event Sessions and Trajectory Sessions, interleaving Filler Sessions to create 160K-token histories per user.

  3. 03

    Evidence Annotation

    PRAGMA annotates which Sessions contain necessary evidence for each query, enabling session-level Recall and Exact Recall evaluation of retrieval systems.

  4. 04

    Response Evaluation

    PRAGMA scores generated guidance with alignment and grounding rubrics, using LLM judges to assess whether responses match trajectories and cite annotated evidence.

KEY CONTRIBUTIONS

Key Contributions

  • 01

    PRAGMA benchmark introduction

    PRAGMA provides 100 users, 400 queries, and about 160K conversational tokens per user, covering Event-Align, Event-Correct, Traj-Align, and Traj-Correct guidance scenarios.

  • 02

    Controlled construction pipeline

    PRAGMA uses a controlled pipeline with User Schema, Event Sessions, Trajectory Sessions, and Filler Sessions plus human validation to avoid recency shortcuts and shallow trajectories.

  • 03

    Joint retrieval and guidance evaluation

    PRAGMA evaluates retrieval Recall and Exact Recall alongside alignment and grounding, revealing that Oracle-Summary can reach 99.00 alignment but Oracle-Session lags far behind.

RESULTS

By the Numbers

Alignment Traj-Align Oracle Summary

99.00

+21.00 over Oracle Session gpt-5-mini

Grounding Traj-Align Oracle Summary

86.00

+69.00 over No-Context gpt-5-mini

Alignment Event-Align Oracle Summary

99.00

+15.00 over Oracle Session gpt-5-mini

Grounding Event-Align Oracle Summary

97.00

+58.00 over Oracle Session gpt-5-mini

These metrics come from PRAGMA’s Oracle-Session and Oracle-Summary settings on Event-Align and Traj-Align queries. They show that compressed evidence summaries in PRAGMA dramatically improve guidance quality compared to raw session context, quantifying the memory utilization gap.

BENCHMARK

By the Numbers

These metrics come from PRAGMA’s Oracle-Session and Oracle-Summary settings on Event-Align and Traj-Align queries. They show that compressed evidence summaries in PRAGMA dramatically improve guidance quality compared to raw session context, quantifying the memory utilization gap.

BENCHMARK

Oracle vs No-Context on PRAGMA Traj-Align (gpt-5-mini)

Alignment scores on Traj-Align queries in PRAGMA for different evidence settings.

KEY INSIGHT

The Counterintuitive Finding

On Traj-Align queries, PRAGMA’s Oracle-Summary reaches 99.00 alignment and 86.00 grounding, while Oracle-Session manages only 78.00 alignment and 17.00 grounding.

This is surprising because gold evidence sessions are fully available, yet PRAGMA shows systems still fail to synthesize them without explicit summarization.

WHY IT MATTERS

What this unlocks for the field

PRAGMA unlocks a way to separately stress-test retrieval, memory preservation, and evidence utilization in personalized guidance over long conversations.

With PRAGMA, builders can design memory architectures that optimize not just recall but generation-usable summaries, moving beyond naive long-context conditioning.

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