diff --git a/server/src/__tests__/heartbeat-workspace-session.test.ts b/server/src/__tests__/heartbeat-workspace-session.test.ts
index 83a7149dee..bf2ae5e722 100644
--- a/server/src/__tests__/heartbeat-workspace-session.test.ts
+++ b/server/src/__tests__/heartbeat-workspace-session.test.ts
@@ -1013,6 +1013,73 @@ describe("resolveRuntimeSessionParamsForWorkspace", () => {
     });
     expect(result.warning).toBeNull();
   });
+
+  it("preserves a task_session when the resolved cwd matches the persisted cwd", async () => {
+    const agentId = "agent-123";
+    // Use a real on-disk cwd so realpath resolution succeeds; the interesting
+    // case is that the task_session's cwd is neither project_primary nor the
+    // fallback agent home. The previous implementation dropped it wholesale.
+    const taskSessionCwd = await fs.mkdtemp(path.join(os.tmpdir(), "pcp-tasksess-"));
+    try {
+      const result = resolveRuntimeSessionParamsForWorkspace({
+        agentId,
+        previousSessionParams: {
+          sessionId: "task-session-abc",
+          cwd: taskSessionCwd,
+          workspaceId: "workspace-9",
+        },
+        resolvedWorkspace: buildResolvedWorkspace({
+          cwd: taskSessionCwd,
+          source: "task_session",
+          projectId: null,
+          workspaceId: "workspace-9",
+        }),
+      });
+
+      expect(result.sessionParams).toEqual({
+        sessionId: "task-session-abc",
+        cwd: taskSessionCwd,
+        workspaceId: "workspace-9",
+      });
+      expect(result.warning).toBeNull();
+    } finally {
+      await fs.rm(taskSessionCwd, { recursive: true, force: true });
+    }
+  });
+
+  it("preserves a fallback-home session that was persisted via a symlink to the real fallback dir", async () => {
+    const agentId = "agent-symlink";
+    const realFallbackCwd = resolveDefaultAgentWorkspaceDir(agentId);
+    await fs.mkdir(realFallbackCwd, { recursive: true });
+    const symlinkDir = await fs.mkdtemp(path.join(os.tmpdir(), "pcp-symlink-"));
+    const symlinkPath = path.join(symlinkDir, "fallback-alias");
+    await fs.symlink(realFallbackCwd, symlinkPath);
+    try {
+      const result = resolveRuntimeSessionParamsForWorkspace({
+        agentId,
+        previousSessionParams: {
+          sessionId: "session-symlink",
+          cwd: symlinkPath, // persisted through symlinked path
+          workspaceId: null,
+        },
+        resolvedWorkspace: buildResolvedWorkspace({
+          cwd: realFallbackCwd, // resolver hands back the real fallback path
+          source: "agent_home",
+          projectId: null,
+          workspaceId: null,
+        }),
+      });
+
+      expect(result.sessionParams).toEqual({
+        sessionId: "session-symlink",
+        cwd: symlinkPath,
+        workspaceId: null,
+      });
+      expect(result.warning).toBeNull();
+    } finally {
+      await fs.rm(symlinkDir, { recursive: true, force: true });
+    }
+  });
 });
 
 describe("applyPersistedExecutionWorkspaceConfig", () => {
diff --git a/server/src/services/heartbeat.ts b/server/src/services/heartbeat.ts
index 3101050a8d..6e9e165e44 100644
--- a/server/src/services/heartbeat.ts
+++ b/server/src/services/heartbeat.ts
@@ -1,4 +1,5 @@
 import fs from "node:fs/promises";
+import { realpathSync } from "node:fs";
 import path from "node:path";
 import { execFile as execFileCallback } from "node:child_process";
 import { promisify } from "node:util";
@@ -2473,6 +2474,21 @@ export function parseSessionCompactionPolicy(agent: typeof agents.$inferSelect):
   return resolveSessionCompactionPolicy(agent.adapterType, agent.runtimeConfig).policy;
 }
 
+// Canonicalize a cwd for equality comparison across symlinked paths. The CLI
+// encodes session files under the physical directory it saw, so a persisted
+// cwd captured through a symlink must compare equal to the same physical
+// directory expressed as its real path. Falls back to `path.resolve` when the
+// path does not exist on disk (which is legitimate in unit tests and for
+// prospective/planned cwds).
+function canonicalizeCwdForComparison(target: string): string {
+  const normalized = path.resolve(target);
+  try {
+    return realpathSync(normalized);
+  } catch {
+    return normalized;
+  }
+}
+
 export function resolveRuntimeSessionParamsForWorkspace(input: {
   agentId: string;
   previousSessionParams: Record<string, unknown> | null;
@@ -2487,6 +2503,8 @@ export function resolveRuntimeSessionParamsForWorkspace(input: {
       warning: null as string | null,
     };
   }
+  const canonicalPreviousCwd = canonicalizeCwdForComparison(previousCwd);
+  const canonicalResolvedCwd = canonicalizeCwdForComparison(resolvedWorkspace.cwd);
   // Inverse-of-migration case: the persisted session was captured in a
   // project workspace but the current run resolves to the agent's home
   // workspace (e.g. a timer/heartbeat wake with no active issue while the
@@ -2497,8 +2515,20 @@ export function resolveRuntimeSessionParamsForWorkspace(input: {
   // and the state stays coherent (rather than accumulating stderr warnings
   // while the CLI silently self-heals).
   if (resolvedWorkspace.source !== "project_primary") {
+    // Safe to resume when the resolved cwd matches the persisted cwd — the
+    // session jsonl exists under the same directory. Covers the `task_session`
+    // source where `resolveWorkspaceForRun` deliberately reuses the persisted
+    // session's cwd, and any `agent_home` resolution that lands on the exact
+    // same directory that hosted the session.
+    if (canonicalPreviousCwd === canonicalResolvedCwd) {
+      return {
+        sessionParams: previousSessionParams,
+        warning: null as string | null,
+      };
+    }
     const fallbackAgentHomeCwd = resolveDefaultAgentWorkspaceDir(agentId);
-    if (path.resolve(previousCwd) !== path.resolve(fallbackAgentHomeCwd)) {
+    const canonicalFallbackCwd = canonicalizeCwdForComparison(fallbackAgentHomeCwd);
+    if (canonicalPreviousCwd !== canonicalFallbackCwd) {
       return {
         sessionParams: null,
         warning:
@@ -2520,13 +2550,14 @@ export function resolveRuntimeSessionParamsForWorkspace(input: {
     };
   }
   const fallbackAgentHomeCwd = resolveDefaultAgentWorkspaceDir(agentId);
-  if (path.resolve(previousCwd) !== path.resolve(fallbackAgentHomeCwd)) {
+  const canonicalFallbackCwd = canonicalizeCwdForComparison(fallbackAgentHomeCwd);
+  if (canonicalPreviousCwd !== canonicalFallbackCwd) {
     return {
       sessionParams: previousSessionParams,
       warning: null as string | null,
     };
   }
-  if (path.resolve(projectCwd) === path.resolve(previousCwd)) {
+  if (canonicalizeCwdForComparison(projectCwd) === canonicalPreviousCwd) {
     return {
       sessionParams: previousSessionParams,
       warning: null as string | null,