diff --git a/devlog/2026-07-30_how-to-compress-investigation/REQ.md b/devlog/2026-07-30_how-to-compress-investigation/REQ.md
new file mode 100644
index 0000000..186320d
--- /dev/null
+++ b/devlog/2026-07-30_how-to-compress-investigation/REQ.md
@@ -0,0 +1,21 @@
+# REQ: Re-add HOW_TO_COMPRESS_RULES to nudge injection
+
+## Problem
+
+v1.14.7 (PR #228) removed `HOW_TO_COMPRESS_RULES` from nudge templates and the breakdown block, keeping it only in the system prompt (injected every turn). The rationale was token savings (~2.4-3.6K per nudge turn) and deduplication.
+
+However, in long sessions (8,700+ messages), the system prompt is 12K chars buried at the START of a 1M+ token context. The model's attention to rules in the system prompt degrades significantly — the "lost in the middle" effect. When the nudge fires and the model is about to compress, the detailed summary-writing rules (KEEP VERBATIM, DROP, PRIORITY) are not at high attention where they're needed most.
+
+The nudge message IS at the END of the context (high attention). Before v1.14.7, it contained HOW_TO_COMPRESS_RULES. After v1.14.7, it only contains COMPRESS_PHILOSOPHY (a short 889-char high-level guide) — missing the detailed 4936-char rules for HOW to write good summaries.
+
+## Fix
+
+Re-add HOW_TO_COMPRESS_RULES to the nudge message in two places:
+
+1. **Non-maxLimit path** (`inject.ts:534`): Between COMPRESS_PHILOSOPHY and the compressible ranges list. Only when `recommendedRanges.length > 0` (no point adding rules if nothing to compress).
+
+2. **MaxLimit path** (`inject.ts:545`): In the strong alert tipsText, before the JSON example.
+
+## Tradeoff
+
++5K chars when a nudge fires (gated by nudgeGrowthTokens — not every turn). Better summaries = fewer recompressions needed = net token savings. The rules appear at HIGH attention (end of context) exactly when the model needs them.
diff --git a/devlog/2026-07-30_how-to-compress-investigation/WORKLOG.md b/devlog/2026-07-30_how-to-compress-investigation/WORKLOG.md
new file mode 100644
index 0000000..569a61a
--- /dev/null
+++ b/devlog/2026-07-30_how-to-compress-investigation/WORKLOG.md
@@ -0,0 +1,20 @@
+# WORKLOG: Re-add HOW_TO_COMPRESS_RULES to nudge injection
+
+## 2026-07-30
+
+### Investigation
+- User reported "how to compress" injection getting lost (session ses_0b89319b, floor 8683)
+- Checked deployed bundle: HOW_TO_COMPRESS_RULES IS in system prompt (system.ts:58)
+- Checked debug nudge message: COMPRESS_PHILOSOPHY present but HOW_TO_COMPRESS_RULES missing
+- Root cause: v1.14.7 (PR #228) removed rules from nudge to save tokens; kept in system prompt only
+- "Lost in the middle" effect: system prompt is 12K chars at START of 1M+ token context — low attention
+- Nudge message is at END of context — high attention — but rules are no longer there
+
+### Implementation
+- `inject.ts:44`: Added `HOW_TO_COMPRESS_RULES` to import from cc-alg
+- `inject.ts:534`: Added rules before compressible ranges list (non-maxLimit path)
+- `inject.ts:545`: Added rules to strong alert tipsText (maxLimit path)
+
+### Verification
+- typecheck: clean
+- 934 tests pass (0 failures)
diff --git a/lib/messages/inject/inject.ts b/lib/messages/inject/inject.ts
index 953f823..49564ba 100644
--- a/lib/messages/inject/inject.ts
+++ b/lib/messages/inject/inject.ts
@@ -41,7 +41,7 @@ import {
     resolveAdaptiveNudgeGrowth,
 } from "./utils"
 import { buildCompressedBlockGuidance } from "../../prompts/extensions/nudge"
-import { COMPRESS_PHILOSOPHY, TIER2_DISTILL_RULES, TIER3_CONDENSE_RULES } from "context-compress-algorithms/prompts"
+import { COMPRESS_PHILOSOPHY, HOW_TO_COMPRESS_RULES, TIER2_DISTILL_RULES, TIER3_CONDENSE_RULES } from "context-compress-algorithms/prompts"
 import { getTierTokenUsage } from "../../state/utils"
 
 /**
@@ -532,7 +532,7 @@ export const injectCompressNudges = (
             }
 
             if (recommendedRanges.length > 0) {
-                breakdown += `\n\n${formatCompressibleRanges(recommendedRanges, contextRanges.protected)}`
+                breakdown += `\n\n${HOW_TO_COMPRESS_RULES}\n\n${formatCompressibleRanges(recommendedRanges, contextRanges.protected)}`
                 breakdown += `\n💡 Compress all ranges in one call (pass multiple content entries: \`content: [{...}, {...}]\`).`
             }
             breakdown += `\nUse \`acp_status({scope:"uncompressed"})\` to re-fetch compressible ranges after compressing, or \`acp_status\` for compressed block details.`
@@ -543,7 +543,7 @@ export const injectCompressNudges = (
         // maxLimit strong alert + lastNudgeShownTokens + block aging guidance
         if (effectiveTipsVariant === "maxLimit") {
             tipsText =
-                '\n\n⚠️ Context limit reached — compress now. Prioritize consumed tool outputs.\n\n{ "topic": "...", "content": [{ "startId": "<ID>", "endId": "<ID>", "summary": "..." }] }\n\nOnly use IDs from visible messages above. Compress older work first.'
+                '\n\n⚠️ Context limit reached — compress now. Prioritize consumed tool outputs.\n\n' + HOW_TO_COMPRESS_RULES + '\n\n{ "topic": "...", "content": [{ "startId": "<ID>", "endId": "<ID>", "summary": "..." }] }\n\nOnly use IDs from visible messages above. Compress older work first.'
         }
         // Intentionally do NOT update lastPerMessageNudgeTokens here — nudges
         // repeat every turn until the model actually compresses.