AI Coach connection error prevents starting coaching session for goal creation

[mottych]

Description

When trying to use the Ai to create a new goal user gets a 500 error

Screenshot:

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Website URL:
https://dev.purposepath.app/strategic-planning/goals

Device and browser info:
Chrome 145.0.7632.117 (1047x947) | Windows (x86) 11

Date and time:
April 21st 2026 | 5:57pm UTC

View developer information (console logs, network requests & timing):
jam.dev/c/f5fbd654-cb62-4e69-9498-a342d7b7024a

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Captured with jam.dev

Priority

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[mottych]

Progress (#326)\n\nVerified root cause (CloudWatch): \put_item\ failed with \Float types are not supported. Use Decimal types instead.\ when persisting coaching session \context\ for topic \goals\ (enriched payload contains floats from Traction JSON).\n\nFix: Centralize \convert_floats_to_decimal\ in \shared/services/dynamodb_serialization.py, apply to \DynamoDBCoachingSessionRepository._to_dynamodb_item, reuse from \�sync_execution_service.\n\nValidation: ruff, mypy, pytest (including new serialization tests).

[mottych]

Resolved\n\nRoot cause (CloudWatch): DynamoDB \put_item\ rejected Python \loat\ values in persisted coaching session payloads (\Float types are not supported. Use Decimal types instead.), surfaced as HTTP 500 on \POST /ai/coaching/start\ for topic \goals.\n\nFix (merged to \dev): Recursively convert floats to \Decimal\ in \DynamoDBCoachingSessionRepository._to_dynamodb_item\ via new shared helper \shared/services/dynamodb_serialization.py; \�sync_execution_service\ now imports the same helper.\n\nVerification: ruff + mypy clean; unit tests including \ est_dynamodb_coaching_session_repository.py\ and \ est_async_execution_service\ pass under the coaching venv.