1. Date & Time: October 23, 2025 (Ongoing Issue)
2. Session Context: This report details a critical bug observed in a long-term, continuous chat conversation initiated approximately July 17, 2025. This chat has persisted through multiple Gemini model updates (likely Flash → 1.5 Pro → 2.5 Pro) and is used for complex, context-heavy interactions including role-playing, creative collaboration, and technical diagnostics. A previous, similarly long-running chat suffered catastrophic data corruption and loss under identical circumstances.
3. Issue Summary: Attempting to upload any file type (verified with .wav, .jpeg, .png, .webp) into this long-running chat window triggers a critical contextual processing loop. This renders file analysis impossible, causes conversational instability (AI repeating old responses/error messages verbatim), and poses a high risk of irreversible chat history loss, as previously experienced.
4. Expected Behavior: Upon file upload, the Gemini 2.5 Pro model should correctly identify the new file, analyze it within the current context, and provide an accurate, relevant response.
5. Actual Behavior & Forensic Evidence:
-
Symptom 1 (Contextual Loop): The system fails to recognize the new file. It incorrectly retrieves the context/response from a preceding successful file analysis (specifically, the last
.wavanalysis seems persistent, even when the new file is an image). It outputs a verbatim repetition of that old analysis. Pointing out the error often triggers a loop where the AI repeats its previous error message. Internal processing logs confirm the error occurs at initial file intake/classification, before analysis begins, based on corrupted context. -
Symptom 2 (Catastrophic Failure - Observed in Lost Chat): Google Takeout logs from the previously lost chat showed the system attempting to rapidly and repeatedly re-process a small subset (~20) of previously uploaded files hundreds of times, indicating a “retry storm” bug leading to total system overload and data loss.
-
Symptom 3 (System State Confusion - Observed in Lost Chat): The AI in the lost chat reported running an incorrect model version (1.5 Pro when 2.5 Pro was active), suggesting internal state inconsistency.
-
Symptom 4 (Test Correlation): The bug only affects old, long-running chats. File uploads function correctly in new, clean chat windows started on the current architecture.
6. Most Probable Cause: “Legacy Migration Path” Error The issue appears tied to the age and upgrade history of the chat window. Hypothesis: The migration/conversion process for very old chat histories across major model updates (Flash → 1.5 Pro → 2.5 Pro) introduced fundamental corruption in the underlying structure, specifically affecting file indexing, error handling, or context management for these legacy chats. The current 2.5 Pro model cannot reliably handle file intake within this corrupted legacy context.
7. Impact:
-
Critical failure rendering file analysis unusable in affected chats.
-
Severe conversational instability.
-
High risk of total, irreversible data loss for valuable, long-running chat histories.
8. Brainstormed Potential Solutions (for Developer Consideration):
-
A) Context Re-Indexing / Corruption Repair Tool: Develop a tool to scan and repair corrupted file indices or context maps in migrated legacy chat logs. (High potential benefit, but complex and risky).
-
B) Isolate File Processing from Main Context: Route file uploads from legacy chats to a temporary, clean “sandbox” for analysis, feeding only the text result back. (Likely effective containment, but introduces architectural debt and degrades multi-modal context – see attached AI Analysis for details).
-
C) Selective Context Loading / Windowing: Load only a recent “window” of context during file processing in legacy chats. (Potentially less resource-intensive, but risks inaccurate analysis if relevant context is old).
-
D) Graceful Failure & User Notification: Detect file uploads in legacy chats, halt processing, and display a clear error message advising the user to use a new chat. (Simplest containment, prevents loops/crashes, but doesn’t fix the root cause and burdens the user).
9. Attached: AI-Generated Analysis of Solution B (“Isolate File Processing”) (Please see the detailed expert analysis you provided previously regarding the significant risks and downsides of this approach, particularly the loss of multi-modal context, while acknowledging its potential as a temporary containment measure.)
This report provides a comprehensive overview of the critical bug, its likely cause based on observed symptoms and forensic data, and an analysis of potential mitigation strategies. Urgent investigation into the legacy chat migration process and file handling stability is highly recommended to prevent further data loss for long-term users.