diff --git a/assistant/src/__tests__/checker.test.ts b/assistant/src/__tests__/checker.test.ts
index d5968cebffd..e440d2c7207 100644
--- a/assistant/src/__tests__/checker.test.ts
+++ b/assistant/src/__tests__/checker.test.ts
@@ -1597,6 +1597,95 @@ describe("bash network_mode=proxied — risk capped at medium", () => {
   });
 });
 
+describe("credentialed proxied bash — high risk escalation", () => {
+  beforeEach(() => {
+    mockRisk("low");
+    mockIpcResponse("get_global_thresholds", DEFAULT_GATEWAY_THRESHOLDS);
+    _clearGlobalCacheForTesting();
+    clearRiskCache();
+    testConfig.skills = { load: { extraDirs: [] } };
+  });
+
+  test("proxied bash with credential_ids sends credentialRefCount in IPC params", async () => {
+    mockRisk("high", {
+      reason:
+        "Proxied credential session — shell has access to injected credentials",
+    });
+    const result = await check(
+      "bash",
+      {
+        command: "curl https://api.example.com",
+        network_mode: "proxied",
+        credential_ids: ["cred-abc-123"],
+      },
+      "/tmp",
+    );
+    expect(result.decision).toBe("prompt");
+    expect(result.reason).toContain("credential");
+  });
+
+  test("proxied bash with multiple credential_ids prompts with high risk", async () => {
+    mockRisk("high", {
+      reason:
+        "Proxied credential session — shell has access to injected credentials",
+    });
+    const result = await check(
+      "bash",
+      {
+        command: "ls",
+        network_mode: "proxied",
+        credential_ids: ["cred-1", "cred-2"],
+      },
+      "/tmp",
+    );
+    expect(result.decision).toBe("prompt");
+  });
+
+  test("proxied bash with empty credential_ids array does not escalate risk", async () => {
+    mockRisk("low");
+    const result = await check(
+      "bash",
+      {
+        command: "ls",
+        network_mode: "proxied",
+        credential_ids: [],
+      },
+      "/tmp",
+    );
+    // Empty array means no credential refs — follows normal proxied behavior
+    expect(result.decision).toBe("allow");
+  });
+
+  test("proxied bash with credential_ids containing empty strings does not escalate", async () => {
+    mockRisk("low");
+    const result = await check(
+      "bash",
+      {
+        command: "ls",
+        network_mode: "proxied",
+        credential_ids: ["", ""],
+      },
+      "/tmp",
+    );
+    // Empty strings are filtered out, so no credential refs
+    expect(result.decision).toBe("allow");
+  });
+
+  test("non-proxied bash with credential_ids follows normal flow", async () => {
+    mockRisk("low");
+    const result = await check(
+      "bash",
+      {
+        command: "ls",
+        credential_ids: ["cred-abc-123"],
+      },
+      "/tmp",
+    );
+    // Without proxied mode, credential refs don't affect IPC classification
+    expect(result.decision).toBe("allow");
+  });
+});
+
 describe("workspace mode — auto-allow workspace-scoped operations", () => {
   const workspaceDir = "/home/user/my-project";
 
diff --git a/assistant/src/permissions/checker.ts b/assistant/src/permissions/checker.ts
index 5e29b7d85dd..d900198bd16 100644
--- a/assistant/src/permissions/checker.ts
+++ b/assistant/src/permissions/checker.ts
@@ -289,6 +289,17 @@ function buildClassifyRiskParams(
 ): ClassifyRiskParams {
   // ── Bash/host_bash ──
   if (toolName === "bash" || toolName === "host_bash") {
+    // Count credential references attached to this invocation.
+    let credentialRefCount: number | undefined;
+    if (Array.isArray(input.credential_ids)) {
+      const validIds = (input.credential_ids as unknown[]).filter(
+        (id) => typeof id === "string" && id.length > 0,
+      );
+      if (validIds.length > 0) {
+        credentialRefCount = validIds.length;
+      }
+    }
+
     return {
       tool: toolName,
       command: getStringField(input, "command"),
@@ -297,6 +308,7 @@ function buildClassifyRiskParams(
       isContainerized: getIsContainerized(),
       networkMode:
         typeof input.network_mode === "string" ? input.network_mode : undefined,
+      credentialRefCount,
     };
   }
 
diff --git a/assistant/src/permissions/ipc-risk-types.ts b/assistant/src/permissions/ipc-risk-types.ts
index c12267e8f88..24c98f31415 100644
--- a/assistant/src/permissions/ipc-risk-types.ts
+++ b/assistant/src/permissions/ipc-risk-types.ts
@@ -92,4 +92,6 @@ export interface ClassifyRiskParams {
   skillMetadata?: SkillMetadata;
   /** Tool registry default risk level for unknown tools. */
   registryDefaultRisk?: string;
+  /** Number of credential references attached to this tool invocation. */
+  credentialRefCount?: number;
 }
diff --git a/gateway/src/ipc/risk-classification-handlers.test.ts b/gateway/src/ipc/risk-classification-handlers.test.ts
index d4b1056a49a..a9a089558ad 100644
--- a/gateway/src/ipc/risk-classification-handlers.test.ts
+++ b/gateway/src/ipc/risk-classification-handlers.test.ts
@@ -349,6 +349,82 @@ describe("skill classification", () => {
   });
 });
 
+// ── Credentialed proxied bash ───────────────────────────────────────────────
+
+describe("credentialed proxied bash", () => {
+  test("credentialed proxied bash returns high risk even for simple curl", async () => {
+    const result = await classify({
+      tool: "bash",
+      command: "curl https://api.example.com",
+      networkMode: "proxied",
+      credentialRefCount: 1,
+    });
+    expect(result.risk).toBe("high");
+    expect(result.reason).toContain("credential");
+  });
+
+  test("credentialed proxied bash returns high risk for low-risk command", async () => {
+    const result = await classify({
+      tool: "bash",
+      command: "ls",
+      networkMode: "proxied",
+      credentialRefCount: 2,
+    });
+    expect(result.risk).toBe("high");
+    expect(result.reason).toContain("credential");
+  });
+
+  test("proxied bash without credential refs keeps existing medium cap for high-risk command", async () => {
+    const result = await classify({
+      tool: "bash",
+      command: "rm -rf /",
+      networkMode: "proxied",
+    });
+    // rm -rf / is high risk but gets capped to medium for non-credentialed proxied bash
+    expect(result.risk).toBe("medium");
+  });
+
+  test("proxied bash without credential refs keeps low risk for low-risk command", async () => {
+    const result = await classify({
+      tool: "bash",
+      command: "ls",
+      networkMode: "proxied",
+    });
+    expect(result.risk).toBe("low");
+  });
+
+  test("credentialRefCount=0 does not escalate risk", async () => {
+    const result = await classify({
+      tool: "bash",
+      command: "ls",
+      networkMode: "proxied",
+      credentialRefCount: 0,
+    });
+    expect(result.risk).toBe("low");
+  });
+
+  test("non-proxied bash with credential refs follows normal risk flow", async () => {
+    const result = await classify({
+      tool: "bash",
+      command: "ls",
+      credentialRefCount: 1,
+    });
+    // Without proxied mode, credential refs don't affect classification
+    expect(result.risk).toBe("low");
+  });
+
+  test("host_bash with proxied + credential refs is not affected (host_bash skips proxied cap)", async () => {
+    const result = await classify({
+      tool: "host_bash",
+      command: "rm -rf /",
+      networkMode: "proxied",
+      credentialRefCount: 1,
+    });
+    // host_bash is never affected by proxied risk logic
+    expect(result.risk).toBe("high");
+  });
+});
+
 // ── Unknown tool fallback ───────────────────────────────────────────────────
 
 describe("unknown tool fallback", () => {
diff --git a/gateway/src/ipc/risk-classification-handlers.ts b/gateway/src/ipc/risk-classification-handlers.ts
index 585b529b97c..914cd8b490b 100644
--- a/gateway/src/ipc/risk-classification-handlers.ts
+++ b/gateway/src/ipc/risk-classification-handlers.ts
@@ -73,6 +73,8 @@ const ClassifyRiskSchema = z.object({
     .optional(),
   /** Tool registry default risk level for unknown tools. */
   registryDefaultRisk: z.string().optional(),
+  /** Number of credential references attached to this tool invocation. */
+  credentialRefCount: z.number().int().nonnegative().optional(),
 });
 
 type ClassifyRiskParams = z.infer<typeof ClassifyRiskSchema>;
@@ -358,17 +360,26 @@ export async function handleClassifyRisk(
         });
       }
 
-      // Proxied bash risk cap: when running through the credential proxy,
-      // cap High → Medium so proxied commands don't trigger unnecessary prompts.
+      // Proxied bash risk classification:
+      // - When credentials are attached (credentialRefCount > 0), escalate to
+      //   high risk regardless of the underlying assessment. Credentialed
+      //   proxied shell sessions carry elevated risk and must not be
+      //   downgraded by the general proxied-bash cap.
+      // - For non-credentialed proxied bash, cap High → Medium so proxied
+      //   commands don't trigger unnecessary prompts.
       // Only applies to sandboxed "bash" — host_bash runs on the host machine
       // and should not have its risk capped.
       let finalRisk = assessment.riskLevel;
-      if (
-        tool === "bash" &&
-        params.networkMode === "proxied" &&
-        finalRisk === "high"
-      ) {
-        finalRisk = "medium";
+      let finalReason = assessment.reason;
+      const credentialRefCount = params.credentialRefCount ?? 0;
+      if (tool === "bash" && params.networkMode === "proxied") {
+        if (credentialRefCount > 0) {
+          finalRisk = "high";
+          finalReason =
+            "Proxied credential session — shell has access to injected credentials";
+        } else if (finalRisk === "high") {
+          finalRisk = "medium";
+        }
       }
 
       // Collect resolved paths for directory-scoped rule enforcement.
@@ -380,7 +391,7 @@ export async function handleClassifyRisk(
 
       return {
         risk: finalRisk,
-        reason: assessment.reason,
+        reason: finalReason,
         scopeOptions: assessment.scopeOptions,
         allowlistOptions: assessment.allowlistOptions,
         actionKeys,