diff --git a/docs/reference/policy-engine.md b/docs/reference/policy-engine.md
index 456c8a9dc8..1b9575475a 100644
--- a/docs/reference/policy-engine.md
+++ b/docs/reference/policy-engine.md
@@ -301,7 +301,7 @@ priority = 10
 # (Optional) A custom message to display when a tool call is denied by this
 # rule. This message is returned to the model and user,
 # useful for explaining *why* it was denied.
-deny_message = "Deletion is permanent"
+denyMessage = "Deletion is permanent"
 
 # (Optional) An array of approval modes where this rule is active.
 modes = ["autoEdit"]
@@ -310,6 +310,14 @@ modes = ["autoEdit"]
 # non-interactive (false) environments.
 # If omitted, the rule applies to both.
 interactive = true
+
+# (Optional) If true, lets shell commands use redirection operators
+# (>, >>, <, <<, <<<). By default, the policy engine asks for confirmation
+# when redirection is detected, even if a rule matches the command.
+# This permission is granular; it only applies to the specific rule it's
+# defined in. In chained commands (e.g., cmd1 > file && cmd2), each
+# individual command rule must permit redirection if it's used.
+allowRedirection = true
 ```
 
 ### Using arrays (lists)
@@ -394,7 +402,7 @@ server.
 mcpName = "untrusted-server"
 decision = "deny"
 priority = 500
-deny_message = "This server is not trusted by the admin."
+denyMessage = "This server is not trusted by the admin."
 ```
 
 **3. Targeting all MCP servers**
diff --git a/packages/cli/src/commands/extensions/examples/policies/policies/policies.toml b/packages/cli/src/commands/extensions/examples/policies/policies/policies.toml
index d89d5e5737..225627c59b 100644
--- a/packages/cli/src/commands/extensions/examples/policies/policies/policies.toml
+++ b/packages/cli/src/commands/extensions/examples/policies/policies/policies.toml
@@ -16,7 +16,7 @@ toolName = "grep_search"
 argsPattern = "(\.env|id_rsa|passwd)"
 decision = "deny"
 priority = 200
-deny_message = "Access to sensitive credentials or system files is restricted by the policy-example extension."
+denyMessage = "Access to sensitive credentials or system files is restricted by the policy-example extension."
 
 # Safety Checker: Apply path validation to all write operations.
 [[safety_checker]]
diff --git a/packages/core/src/confirmation-bus/types.ts b/packages/core/src/confirmation-bus/types.ts
index ceb1c96296..70e2d31f6b 100644
--- a/packages/core/src/confirmation-bus/types.ts
+++ b/packages/core/src/confirmation-bus/types.ts
@@ -136,6 +136,7 @@ export interface UpdatePolicy {
   argsPattern?: string;
   commandPrefix?: string | string[];
   mcpName?: string;
+  allowRedirection?: boolean;
 }
 
 export interface ToolPolicyRejection {
diff --git a/packages/core/src/policy/config.ts b/packages/core/src/policy/config.ts
index c54e7f1667..f6107bf460 100644
--- a/packages/core/src/policy/config.ts
+++ b/packages/core/src/policy/config.ts
@@ -537,6 +537,7 @@ interface TomlRule {
   priority?: number;
   commandPrefix?: string | string[];
   argsPattern?: string;
+  allowRedirection?: boolean;
   // Index signature to satisfy Record type if needed for toml.stringify
   [key: string]: unknown;
 }
@@ -581,6 +582,7 @@ export function createPolicyUpdater(
               argsPattern: new RegExp(pattern),
               mcpName: message.mcpName,
               source: 'Dynamic (Confirmed)',
+              allowRedirection: message.allowRedirection,
             });
           }
         }
@@ -617,6 +619,7 @@ export function createPolicyUpdater(
           argsPattern,
           mcpName: message.mcpName,
           source: 'Dynamic (Confirmed)',
+          allowRedirection: message.allowRedirection,
         });
       }
 
@@ -681,6 +684,10 @@ export function createPolicyUpdater(
               newRule.argsPattern = message.argsPattern;
             }
 
+            if (message.allowRedirection !== undefined) {
+              newRule.allowRedirection = message.allowRedirection;
+            }
+
             // Add to rules
             existingData.rule.push(newRule);
 
diff --git a/packages/core/src/policy/persistence.test.ts b/packages/core/src/policy/persistence.test.ts
index da39160020..d4781fb4be 100644
--- a/packages/core/src/policy/persistence.test.ts
+++ b/packages/core/src/policy/persistence.test.ts
@@ -71,6 +71,26 @@ describe('createPolicyUpdater', () => {
     expect(content).toContain(`priority = ${expectedPriority}`);
   });
 
+  it('should include allowRedirection when persisting policy', async () => {
+    createPolicyUpdater(policyEngine, messageBus, mockStorage);
+
+    const policyFile = '/mock/user/.gemini/policies/auto-saved.toml';
+    vi.spyOn(mockStorage, 'getAutoSavedPolicyPath').mockReturnValue(policyFile);
+
+    await messageBus.publish({
+      type: MessageBusType.UPDATE_POLICY,
+      toolName: 'test_tool',
+      persist: true,
+      allowRedirection: true,
+    });
+
+    await vi.advanceTimersByTimeAsync(100);
+
+    const content = memfs.readFileSync(policyFile, 'utf-8') as string;
+    expect(content).toContain('toolName = "test_tool"');
+    expect(content).toContain('allowRedirection = true');
+  });
+
   it('should not persist policy when persist flag is false or undefined', async () => {
     createPolicyUpdater(policyEngine, messageBus, mockStorage);
 
diff --git a/packages/core/src/policy/policies/memory-manager.toml b/packages/core/src/policy/policies/memory-manager.toml
index 2055fcdf3a..b1b1b4ddd9 100644
--- a/packages/core/src/policy/policies/memory-manager.toml
+++ b/packages/core/src/policy/policies/memory-manager.toml
@@ -7,4 +7,4 @@ toolName = ["read_file", "write_file", "replace", "list_directory", "glob", "gre
 decision = "allow"
 priority = 100
 argsPattern = "(^|.*/)\\.gemini/.*"
-deny_message = "Memory Manager is only allowed to access the .gemini folder."
+denyMessage = "Memory Manager is only allowed to access the .gemini folder."
diff --git a/packages/core/src/policy/policies/plan.toml b/packages/core/src/policy/policies/plan.toml
index 5a7ee6e59f..b9efd50db7 100644
--- a/packages/core/src/policy/policies/plan.toml
+++ b/packages/core/src/policy/policies/plan.toml
@@ -46,7 +46,7 @@ toolName = "enter_plan_mode"
 decision = "deny"
 priority = 70
 modes = ["plan"]
-deny_message = "You are already in Plan Mode."
+denyMessage = "You are already in Plan Mode."
 
 [[rule]]
 toolName = "exit_plan_mode"
@@ -65,7 +65,7 @@ interactive = false
 toolName = "exit_plan_mode"
 decision = "deny"
 priority = 50
-deny_message = "You are not currently in Plan Mode. Use enter_plan_mode first to design a plan."
+denyMessage = "You are not currently in Plan Mode. Use enter_plan_mode first to design a plan."
 
 
 # Catch-All: Deny everything by default in Plan mode.
@@ -74,7 +74,7 @@ deny_message = "You are not currently in Plan Mode. Use enter_plan_mode first to
 decision = "deny"
 priority = 60
 modes = ["plan"]
-deny_message = "You are in Plan Mode with access to read-only tools. Execution of scripts (including those from skills) is blocked."
+denyMessage = "You are in Plan Mode with access to read-only tools. Execution of scripts (including those from skills) is blocked."
 
 # Explicitly Allow Read-Only Tools in Plan mode.
 
@@ -121,4 +121,4 @@ toolName = ["write_file", "replace"]
 decision = "deny"
 priority = 65
 modes = ["plan"]
-deny_message = "You are in Plan Mode and cannot modify source code. You may ONLY use write_file or replace to save plans to the designated plans directory as .md files."
+denyMessage = "You are in Plan Mode and cannot modify source code. You may ONLY use write_file or replace to save plans to the designated plans directory as .md files."
diff --git a/packages/core/src/policy/policies/yolo.toml b/packages/core/src/policy/policies/yolo.toml
index 230b4c2670..0516484acd 100644
--- a/packages/core/src/policy/policies/yolo.toml
+++ b/packages/core/src/policy/policies/yolo.toml
@@ -52,4 +52,4 @@ interactive = true
 decision = "allow"
 priority = 998
 modes = ["yolo"]
-allow_redirection = true
+allowRedirection = true
diff --git a/packages/core/src/policy/policy-updater.test.ts b/packages/core/src/policy/policy-updater.test.ts
index 3bf3579bbc..5ee9d65df4 100644
--- a/packages/core/src/policy/policy-updater.test.ts
+++ b/packages/core/src/policy/policy-updater.test.ts
@@ -26,6 +26,7 @@ vi.mock('../config/storage.js');
 vi.mock('../utils/shell-utils.js', () => ({
   getCommandRoots: vi.fn(),
   stripShellWrapper: vi.fn(),
+  hasRedirection: vi.fn(),
 }));
 interface ParsedPolicy {
   rule?: Array<{
@@ -177,6 +178,25 @@ describe('createPolicyUpdater', () => {
     );
   });
 
+  it('should pass allowRedirection to policyEngine.addRule', async () => {
+    createPolicyUpdater(policyEngine, messageBus, mockStorage);
+
+    await messageBus.publish({
+      type: MessageBusType.UPDATE_POLICY,
+      toolName: 'run_shell_command',
+      commandPrefix: 'ls',
+      persist: false,
+      allowRedirection: true,
+    });
+
+    expect(policyEngine.addRule).toHaveBeenCalledWith(
+      expect.objectContaining({
+        toolName: 'run_shell_command',
+        allowRedirection: true,
+      }),
+    );
+  });
+
   it('should persist multiple rules correctly to TOML', async () => {
     createPolicyUpdater(policyEngine, messageBus, mockStorage);
     vi.mocked(fs.readFile).mockRejectedValue({ code: 'ENOENT' });
@@ -238,6 +258,7 @@ describe('ShellToolInvocation Policy Update', () => {
     vi.mocked(shellUtils.stripShellWrapper).mockImplementation(
       (c: string) => c,
     );
+    vi.mocked(shellUtils.hasRedirection).mockReturnValue(false);
   });
 
   it('should extract multiple root commands for chained commands', () => {
@@ -279,4 +300,26 @@ describe('ShellToolInvocation Policy Update', () => {
     expect(options!.commandPrefix).toEqual(['ls']);
     expect(shellUtils.getCommandRoots).toHaveBeenCalledWith('ls -la /tmp');
   });
+
+  it('should include allowRedirection if command has redirection', () => {
+    vi.mocked(shellUtils.getCommandRoots).mockReturnValue(['echo']);
+    vi.mocked(shellUtils.hasRedirection).mockReturnValue(true);
+
+    const invocation = new ShellToolInvocation(
+      mockConfig,
+      { command: 'echo "hello" > file.txt' },
+      mockMessageBus,
+      'run_shell_command',
+      'Shell',
+    );
+
+    const options = (
+      invocation as unknown as TestableShellToolInvocation
+    ).getPolicyUpdateOptions(ToolConfirmationOutcome.ProceedAlways);
+    expect(options!.commandPrefix).toEqual(['echo']);
+    expect(options!.allowRedirection).toBe(true);
+    expect(shellUtils.hasRedirection).toHaveBeenCalledWith(
+      'echo "hello" > file.txt',
+    );
+  });
 });
diff --git a/packages/core/src/policy/toml-loader.test.ts b/packages/core/src/policy/toml-loader.test.ts
index 959f09ba80..224450f2a2 100644
--- a/packages/core/src/policy/toml-loader.test.ts
+++ b/packages/core/src/policy/toml-loader.test.ts
@@ -263,6 +263,20 @@ allow_redirection = true
       expect(result.errors).toHaveLength(0);
     });
 
+    it('should parse and transform allowRedirection property (camelCase)', async () => {
+      const result = await runLoadPoliciesFromToml(`
+[[rule]]
+toolName = "run_shell_command"
+commandPrefix = "echo"
+decision = "allow"
+priority = 100
+allowRedirection = true
+`);
+
+      expect(result.rules).toHaveLength(1);
+      expect(result.rules[0].allowRedirection).toBe(true);
+      expect(result.errors).toHaveLength(0);
+    });
     it('should parse deny_message property', async () => {
       const result = await runLoadPoliciesFromToml(`
 [[rule]]
@@ -273,7 +287,21 @@ deny_message = "Deletion is permanent"
 `);
 
       expect(result.rules).toHaveLength(1);
-      expect(result.rules[0].toolName).toBe('rm');
+      expect(result.rules[0].decision).toBe(PolicyDecision.DENY);
+      expect(result.rules[0].denyMessage).toBe('Deletion is permanent');
+      expect(getErrors(result)).toHaveLength(0);
+    });
+
+    it('should parse denyMessage property (camelCase)', async () => {
+      const result = await runLoadPoliciesFromToml(`
+[[rule]]
+toolName = "rm"
+decision = "deny"
+priority = 100
+denyMessage = "Deletion is permanent"
+`);
+
+      expect(result.rules).toHaveLength(1);
       expect(result.rules[0].decision).toBe(PolicyDecision.DENY);
       expect(result.rules[0].denyMessage).toBe('Deletion is permanent');
       expect(getErrors(result)).toHaveLength(0);
diff --git a/packages/core/src/policy/toml-loader.ts b/packages/core/src/policy/toml-loader.ts
index f5210954f7..7f52dacc9f 100644
--- a/packages/core/src/policy/toml-loader.ts
+++ b/packages/core/src/policy/toml-loader.ts
@@ -63,8 +63,10 @@ const PolicyRuleSchema = z.object({
   modes: z.array(z.nativeEnum(ApprovalMode)).optional(),
   interactive: z.boolean().optional(),
   toolAnnotations: z.record(z.any()).optional(),
-  allow_redirection: z.boolean().optional(),
-  deny_message: z.string().optional(),
+  allowRedirection: z.boolean().optional(),
+  allow_redirection: z.boolean().optional(), // deprecated snake_case for backward compatibility
+  denyMessage: z.string().optional(),
+  deny_message: z.string().optional(), // deprecated snake_case for backward compatibility
 });
 
 /**
@@ -478,9 +480,10 @@ export async function loadPoliciesFromToml(
                   modes: rule.modes,
                   interactive: rule.interactive,
                   toolAnnotations: rule.toolAnnotations,
-                  allowRedirection: rule.allow_redirection,
+                  allowRedirection:
+                    rule.allowRedirection ?? rule.allow_redirection,
                   source: `${tierName.charAt(0).toUpperCase() + tierName.slice(1)}: ${file}`,
-                  denyMessage: rule.deny_message,
+                  denyMessage: rule.denyMessage ?? rule.deny_message,
                 };
 
                 // Compile regex pattern
diff --git a/packages/core/src/tools/shell.ts b/packages/core/src/tools/shell.ts
index 8917d281bd..5ae3948559 100644
--- a/packages/core/src/tools/shell.ts
+++ b/packages/core/src/tools/shell.ts
@@ -100,10 +100,12 @@ export class ShellToolInvocation extends BaseToolInvocation<
     ) {
       const command = stripShellWrapper(this.params.command);
       const rootCommands = [...new Set(getCommandRoots(command))];
+      const allowRedirection = hasRedirection(command) ? true : undefined;
+
       if (rootCommands.length > 0) {
-        return { commandPrefix: rootCommands };
+        return { commandPrefix: rootCommands, allowRedirection };
       }
-      return { commandPrefix: this.params.command };
+      return { commandPrefix: this.params.command, allowRedirection };
     }
     return undefined;
   }
diff --git a/packages/core/src/tools/tools.ts b/packages/core/src/tools/tools.ts
index 8b7d7223bd..38f484fba3 100644
--- a/packages/core/src/tools/tools.ts
+++ b/packages/core/src/tools/tools.ts
@@ -138,6 +138,7 @@ export interface PolicyUpdateOptions {
   commandPrefix?: string | string[];
   mcpName?: string;
   toolName?: string;
+  allowRedirection?: boolean;
 }
 
 /**
diff --git a/packages/core/src/utils/shell-utils.test.ts b/packages/core/src/utils/shell-utils.test.ts
index 933ca84817..2370aa25c4 100644
--- a/packages/core/src/utils/shell-utils.test.ts
+++ b/packages/core/src/utils/shell-utils.test.ts
@@ -19,6 +19,7 @@ import {
   getShellConfiguration,
   initializeShellParsers,
   parseCommandDetails,
+  splitCommands,
   stripShellWrapper,
   hasRedirection,
   resolveExecutable,
@@ -304,6 +305,40 @@ describeWindowsOnly('PowerShell integration', () => {
   });
 });
 
+describe('splitCommands', () => {
+  it('should split chained commands', () => {
+    expect(splitCommands('ls -l && git status')).toEqual([
+      'ls -l',
+      'git status',
+    ]);
+  });
+
+  it('should filter out redirection tokens but keep command parts', () => {
+    // Standard redirection
+    expect(splitCommands('echo "hello" > file.txt')).toEqual(['echo "hello"']);
+    expect(splitCommands('printf "test" >> log.txt')).toEqual([
+      'printf "test"',
+    ]);
+    expect(splitCommands('cat < input.txt')).toEqual(['cat']);
+
+    // Heredoc/Herestring
+    expect(splitCommands('cat << EOF\nhello\nEOF')).toEqual(['cat']);
+    // Note: The Tree-sitter bash parser includes the herestring in the main
+    // command node's text, unlike standard redirections which are siblings.
+    expect(splitCommands('grep "foo" <<< "foobar"')).toEqual([
+      'grep "foo" <<< "foobar"',
+    ]);
+  });
+
+  it('should extract nested commands from process substitution while filtering the redirection operator', () => {
+    // This is the key security test: we want cat to be checked, but not the > >(...) wrapper part
+    const parts = splitCommands('echo "foo" > >(cat)');
+    expect(parts).toContain('echo "foo"');
+    expect(parts).toContain('cat');
+    expect(parts.some((p) => p.includes('>'))).toBe(false);
+  });
+});
+
 describe('stripShellWrapper', () => {
   it('should strip sh -c with quotes', () => {
     expect(stripShellWrapper('sh -c "ls -l"')).toEqual('ls -l');
diff --git a/packages/core/src/utils/shell-utils.ts b/packages/core/src/utils/shell-utils.ts
index d2b28a348c..14fce36a34 100644
--- a/packages/core/src/utils/shell-utils.ts
+++ b/packages/core/src/utils/shell-utils.ts
@@ -663,7 +663,10 @@ export function splitCommands(command: string): string[] {
     return [];
   }
 
-  return parsed.details.map((detail) => detail.text).filter(Boolean);
+  return parsed.details
+    .filter((detail) => !REDIRECTION_NAMES.has(detail.name))
+    .map((detail) => detail.text)
+    .filter(Boolean);
 }
 
 /**