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push_strategy fallback should split content intelligently, not dump everything to attachment #31

Description

@jwm4

Problem

When push_strategy.py encounters Jira's CONTENT_LIMIT_EXCEEDED error, it falls back to putting the entire strategy in an attachment and leaving only a TL;DR stub in the Jira description. This makes the Feature description nearly useless for anyone viewing it in Jira.

Expected behavior

The fallback should split the strategy into core content (TL;DR, Technical Approach, Components, Acceptance Criteria, Effort Estimate, Risks) that stays in the description, and supplemental content (Staff Engineer Input, detailed subsections, revision history) that goes to an attachment. Ideally, the skill should present the proposed split to the user for confirmation rather than deciding silently.

How we hit this

RHAISTRAT-1630 grew large after multiple rounds of Staff Engineer Input during human review. The strategy section alone was 65,765 chars ADF, exceeding Jira's limit. The fallback silently moved everything to an attachment.

Suggested approach

  1. When CONTENT_LIMIT_EXCEEDED is hit, identify which sections are largest
  2. Propose a split to the user: "The strategy exceeds Jira's limit. I can keep [sections] in the description and attach [sections] as a file. OK?"
  3. Keep the most-referenced sections inline so the Feature is readable in Jira

Filed by Bill Murdock with assistance from Claude Code.

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