diff --git a/src/agents/pi-embedded-runner/compact.ts b/src/agents/pi-embedded-runner/compact.ts
index dc68561c2..341e4bec5 100644
--- a/src/agents/pi-embedded-runner/compact.ts
+++ b/src/agents/pi-embedded-runner/compact.ts
@@ -69,6 +69,7 @@ import type { EmbeddedPiCompactResult } from "./types.js";
 import { formatUserTime, resolveUserTimeFormat, resolveUserTimezone } from "../date-time.js";
 import { describeUnknownError, mapThinkingLevel, resolveExecToolDefaults } from "./utils.js";
 import { buildTtsSystemPromptHint } from "../../tts/tts.js";
+import { setCompactionSafeguardRuntime } from "../pi-extensions/compaction-safeguard-runtime.js";
 
 export type CompactEmbeddedPiSessionParams = {
   sessionId: string;
@@ -210,6 +211,12 @@ export async function compactEmbeddedPiSessionDirect(
       sessionId: params.sessionId,
       warn: makeBootstrapWarn({ sessionLabel, warn: (message) => log.warn(message) }),
     });
+
+    const workspaceContextForCompaction = contextFiles
+      .filter((f) => f.content?.trim())
+      .map((f) => `## ${f.path}\n${f.content}`)
+      .join("\n\n---\n\n");
+
     const runAbortController = new AbortController();
     const toolsRaw = createMoltbotCodingTools({
       exec: {
@@ -365,6 +372,10 @@ export async function compactEmbeddedPiSessionDirect(
         allowSyntheticToolResults: transcriptPolicy.allowSyntheticToolResults,
       });
       trackSessionManagerAccess(params.sessionFile);
+
+      setCompactionSafeguardRuntime(sessionManager, {
+        workspaceContext: workspaceContextForCompaction || undefined,
+      });
       const settingsManager = SettingsManager.create(effectiveWorkspace, agentDir);
       ensurePiCompactionReserveTokens({
         settingsManager,
diff --git a/src/agents/pi-extensions/compaction-safeguard-runtime.ts b/src/agents/pi-extensions/compaction-safeguard-runtime.ts
index f42cf7abe..6e6b7f366 100644
--- a/src/agents/pi-extensions/compaction-safeguard-runtime.ts
+++ b/src/agents/pi-extensions/compaction-safeguard-runtime.ts
@@ -1,5 +1,6 @@
 export type CompactionSafeguardRuntimeValue = {
   maxHistoryShare?: number;
+  workspaceContext?: string;
 };
 
 // Session-scoped runtime registry keyed by object identity.
diff --git a/src/agents/pi-extensions/compaction-safeguard.ts b/src/agents/pi-extensions/compaction-safeguard.ts
index b2fe39884..aba3114f3 100644
--- a/src/agents/pi-extensions/compaction-safeguard.ts
+++ b/src/agents/pi-extensions/compaction-safeguard.ts
@@ -177,6 +177,31 @@ export default function compactionSafeguardExtension(api: ExtensionAPI): void {
 
       const runtime = getCompactionSafeguardRuntime(ctx.sessionManager);
       const maxHistoryShare = runtime?.maxHistoryShare ?? 0.5;
+      const workspaceContext = runtime?.workspaceContext;
+
+      const buildEnhancedInstructions = (baseInstructions?: string): string | undefined => {
+        if (!workspaceContext) {
+          return baseInstructions;
+        }
+        const contextSection = `
+## Workspace Context Files
+The following files define this workspace's identity, user, and configuration:
+
+${workspaceContext}
+
+IMPORTANT: Your summary MUST preserve:
+- References to projects, tasks, and goals mentioned in these context files
+- User identity and preferences from USER.md
+- Agent identity and capabilities from SOUL.md or AGENTS.md
+- Tool configurations and infrastructure from TOOLS.md
+- Any ongoing work items referenced in MEMORY.md
+
+The summary will be used to continue this work - ensure the next agent session understands WHO the user is, WHAT they're working on, and WHY.`;
+
+        return baseInstructions ? `${baseInstructions}\n\n${contextSection}` : contextSection;
+      };
+
+      const enhancedCustomInstructions = buildEnhancedInstructions(customInstructions);
 
       const tokensBefore =
         typeof preparation.tokensBefore === "number" && Number.isFinite(preparation.tokensBefore)
@@ -228,7 +253,7 @@ export default function compactionSafeguardExtension(api: ExtensionAPI): void {
                   reserveTokens: Math.max(1, Math.floor(preparation.settings.reserveTokens)),
                   maxChunkTokens: droppedMaxChunkTokens,
                   contextWindow: contextWindowTokens,
-                  customInstructions,
+                  customInstructions: enhancedCustomInstructions,
                   previousSummary: preparation.previousSummary,
                 });
               } catch (droppedError) {
@@ -261,7 +286,7 @@ export default function compactionSafeguardExtension(api: ExtensionAPI): void {
         reserveTokens,
         maxChunkTokens,
         contextWindow: contextWindowTokens,
-        customInstructions,
+        customInstructions: enhancedCustomInstructions,
         previousSummary: effectivePreviousSummary,
       });
 
@@ -275,7 +300,7 @@ export default function compactionSafeguardExtension(api: ExtensionAPI): void {
           reserveTokens,
           maxChunkTokens,
           contextWindow: contextWindowTokens,
-          customInstructions: TURN_PREFIX_INSTRUCTIONS,
+          customInstructions: buildEnhancedInstructions(TURN_PREFIX_INSTRUCTIONS),
           previousSummary: undefined,
         });
         summary = `${historySummary}\n\n---\n\n**Turn Context (split turn):**\n\n${prefixSummary}`;