diff --git a/open-sse/handlers/chatCore.ts b/open-sse/handlers/chatCore.ts
index 2f1773bcb4..9759e1e967 100644
--- a/open-sse/handlers/chatCore.ts
+++ b/open-sse/handlers/chatCore.ts
@@ -1689,6 +1689,18 @@ export async function handleChatCore({
               try {
                 const { insertCompressionAnalyticsRow } =
                   await import("../../src/lib/db/compressionAnalytics.ts");
+                const { calculateCost } = await import("../../src/lib/usage/costCalculator.ts");
+                const tokensSaved = Math.max(
+                  0,
+                  result.stats.originalTokens - result.stats.compressedTokens
+                );
+                const estimatedUsdSaved = await calculateCost(
+                  provider ?? "",
+                  effectiveModel ?? "",
+                  {
+                    input: tokensSaved,
+                  }
+                );
                 insertCompressionAnalyticsRow({
                   timestamp: new Date().toISOString(),
                   combo_id: comboName ?? null,
@@ -1696,12 +1708,10 @@ export async function handleChatCore({
                   mode,
                   original_tokens: result.stats.originalTokens,
                   compressed_tokens: result.stats.compressedTokens,
-                  tokens_saved: Math.max(
-                    0,
-                    result.stats.originalTokens - result.stats.compressedTokens
-                  ),
+                  tokens_saved: tokensSaved,
                   duration_ms: result.stats.durationMs ?? null,
                   request_id: skillRequestId,
+                  estimated_usd_saved: estimatedUsdSaved || null,
                   validation_fallback: result.stats.fallbackApplied ? 1 : 0,
                   output_mode: cavemanOutputModeApplied ? cavemanOutputModeIntensity : null,
                 });
diff --git a/open-sse/services/compression/aggressive.ts b/open-sse/services/compression/aggressive.ts
index 83c1acb86c..a1edf3536a 100644
--- a/open-sse/services/compression/aggressive.ts
+++ b/open-sse/services/compression/aggressive.ts
@@ -144,7 +144,10 @@ export function compressAggressive(
     }
 
     try {
-      const liteResult = applyLiteCompression({ messages: currentMessages });
+      const liteResult = applyLiteCompression(
+        { messages: currentMessages },
+        { preserveSystemPrompt: cfg.preserveSystemPrompt !== false }
+      );
       if (liteResult?.compressed && liteResult.stats) {
         const liteSavings = liteResult.stats.savingsPercent ?? 0;
         if (liteSavings > resultStats.savingsPercent) {
diff --git a/open-sse/services/compression/cavemanRules.ts b/open-sse/services/compression/cavemanRules.ts
index 7050372ef3..906f64fc28 100644
--- a/open-sse/services/compression/cavemanRules.ts
+++ b/open-sse/services/compression/cavemanRules.ts
@@ -406,11 +406,15 @@ export function getRuleByName(name: string): CavemanRule | undefined {
 }
 
 export function getCavemanRuleMetadata() {
+  const intensities = ["lite", "full", "ultra"] as const;
   return CAVEMAN_RULES.map((rule) => ({
     name: rule.name,
     context: rule.context,
     category: rule.category ?? "terse",
     minIntensity: rule.minIntensity ?? "lite",
+    intensities: intensities.filter(
+      (intensity) => INTENSITY_RANK[intensity] >= INTENSITY_RANK[rule.minIntensity ?? "lite"]
+    ),
     description: rule.description ?? rule.name.replace(/_/g, " "),
   }));
 }
diff --git a/src/app/(dashboard)/dashboard/settings/components/CompressionSettingsTab.tsx b/src/app/(dashboard)/dashboard/settings/components/CompressionSettingsTab.tsx
index c072e37acf..7d363e817f 100644
--- a/src/app/(dashboard)/dashboard/settings/components/CompressionSettingsTab.tsx
+++ b/src/app/(dashboard)/dashboard/settings/components/CompressionSettingsTab.tsx
@@ -70,6 +70,7 @@ interface RuleMetadata {
   category: string;
   context: string;
   minIntensity: CavemanIntensity;
+  intensities?: CavemanIntensity[];
   description: string;
 }
 
@@ -498,7 +499,7 @@ export default function CompressionSettingsTab() {
                         <button
                           key={rule.name}
                           onClick={() => toggleCavemanRule(rule.name)}
-                          title={`${rule.category} · ${rule.context} · ${rule.minIntensity}`}
+                          title={`${rule.category} · ${rule.context} · ${(rule.intensities ?? [rule.minIntensity]).join("/")}`}
                           className={`px-2 py-1 rounded text-xs border transition-all ${
                             config.cavemanConfig!.skipRules.includes(rule.name)
                               ? "border-red-500/50 bg-red-500/10 text-red-400 line-through"
diff --git a/src/app/api/settings/compression/rules/route.ts b/src/app/api/settings/compression/rules/route.ts
new file mode 100644
index 0000000000..7394c776be
--- /dev/null
+++ b/src/app/api/settings/compression/rules/route.ts
@@ -0,0 +1 @@
+export { GET } from "@/app/api/compression/rules/route";
diff --git a/tests/unit/compression/caveman-v379.test.ts b/tests/unit/compression/caveman-v379.test.ts
index a5f04c3ceb..04a777d18f 100644
--- a/tests/unit/compression/caveman-v379.test.ts
+++ b/tests/unit/compression/caveman-v379.test.ts
@@ -1,7 +1,10 @@
 import { describe, it } from "node:test";
 import assert from "node:assert/strict";
 import { cavemanCompress } from "../../../open-sse/services/compression/caveman.ts";
-import { getRuleByName } from "../../../open-sse/services/compression/cavemanRules.ts";
+import {
+  getCavemanRuleMetadata,
+  getRuleByName,
+} from "../../../open-sse/services/compression/cavemanRules.ts";
 import { applyCompression } from "../../../open-sse/services/compression/strategySelector.ts";
 
 function compress(content: string, options = {}) {
@@ -132,6 +135,7 @@ describe("Caveman v3.7.9 rule parity", () => {
   });
 
   it("exposes metadata for new rule names", () => {
+    const metadata = getCavemanRuleMetadata();
     for (const ruleName of [
       "articles",
       "pleasantries",
@@ -140,6 +144,9 @@ describe("Caveman v3.7.9 rule parity", () => {
       "ultra_abbreviations",
     ]) {
       assert.ok(getRuleByName(ruleName), `missing rule ${ruleName}`);
+      const rule = metadata.find((entry) => entry.name === ruleName);
+      assert.ok(rule?.category, `missing metadata category for ${ruleName}`);
+      assert.ok(rule?.intensities?.length, `missing metadata intensities for ${ruleName}`);
     }
   });
 });
diff --git a/tests/unit/compression/compression-aggressive.test.ts b/tests/unit/compression/compression-aggressive.test.ts
index 2211a70cf5..3a767bf7b0 100644
--- a/tests/unit/compression/compression-aggressive.test.ts
+++ b/tests/unit/compression/compression-aggressive.test.ts
@@ -148,6 +148,26 @@ describe("Integration: strategySelector → aggressive pipeline", () => {
     assert.equal(systemMsg!.content, "You are a helpful coding assistant.");
   });
 
+  it("compressAggressive preserves duplicate system prompts during lite fallback", () => {
+    const messages = [
+      { role: "system", content: "Policy exact. Keep exact." },
+      { role: "system", content: "Policy exact. Keep exact." },
+      { role: "user", content: "Short" },
+    ];
+
+    const result = compressAggressive(messages, {
+      preserveSystemPrompt: true,
+      minSavingsThreshold: 0.9,
+      summarizerEnabled: false,
+      maxTokensPerMessage: 999999,
+    });
+
+    assert.deepEqual(
+      result.messages.filter((message) => message.role === "system"),
+      messages.filter((message) => message.role === "system")
+    );
+  });
+
   it("compressAggressive downgrade chain works when aggressive fails", () => {
     // Empty messages should trigger downgrade gracefully
     const result = compressAggressive([]);
diff --git a/tests/unit/compression/compressionAnalytics.test.ts b/tests/unit/compression/compressionAnalytics.test.ts
index 0490ad8326..b4877c95dc 100644
--- a/tests/unit/compression/compressionAnalytics.test.ts
+++ b/tests/unit/compression/compressionAnalytics.test.ts
@@ -293,6 +293,23 @@ describe("compressionAnalytics", () => {
     assert.equal(summary.realUsage.bySource.provider, 1);
   });
 
+  it("aggregates estimated USD savings separately from token estimates", () => {
+    insertCompressionAnalyticsRow({
+      timestamp: new Date().toISOString(),
+      mode: "standard",
+      original_tokens: 1000,
+      compressed_tokens: 700,
+      tokens_saved: 300,
+      request_id: "req-usd",
+      estimated_usd_saved: 0.0015,
+    });
+    attachCompressionUsageReceipt("req-usd", { prompt_tokens: 700, total_tokens: 700 }, "provider");
+
+    const summary = getCompressionAnalyticsSummary();
+    assert.equal(summary.realUsage.requestsWithReceipts, 1);
+    assert.equal(summary.realUsage.estimatedUsdSaved, 0.0015);
+  });
+
   it("summarizes validation fallback and output mode rows", () => {
     insertCompressionAnalyticsRow({
       timestamp: new Date().toISOString(),