diff --git a/codex-rs/core/src/tools/runtimes/mod.rs b/codex-rs/core/src/tools/runtimes/mod.rs
index a55f78f8a..073fda8ec 100644
--- a/codex-rs/core/src/tools/runtimes/mod.rs
+++ b/codex-rs/core/src/tools/runtimes/mod.rs
@@ -6,6 +6,7 @@ small and focused and reuses the orchestrator for approvals + sandbox + retry.
 */
 use crate::exec_env::CODEX_THREAD_ID_ENV_VAR;
 use crate::path_utils;
+use crate::sandboxing::SandboxPermissions;
 use crate::shell::Shell;
 use crate::tools::sandboxing::ToolError;
 #[cfg(target_os = "macos")]
@@ -43,6 +44,29 @@ pub(crate) fn build_sandbox_command(
     })
 }
 
+pub(crate) fn exec_env_for_sandbox_permissions(
+    env: &HashMap<String, String>,
+    sandbox_permissions: SandboxPermissions,
+) -> HashMap<String, String> {
+    let mut env = env.clone();
+    if sandbox_permissions.requires_escalated_permissions()
+        && env.contains_key(PROXY_ACTIVE_ENV_KEY)
+    {
+        for key in PROXY_ENV_KEYS {
+            env.remove(*key);
+        }
+        // Only macOS injects a Codex-owned SSH wrapper for the managed SOCKS proxy.
+        #[cfg(target_os = "macos")]
+        if env
+            .get(PROXY_GIT_SSH_COMMAND_ENV_KEY)
+            .is_some_and(|command| command.starts_with(CODEX_PROXY_GIT_SSH_COMMAND_MARKER))
+        {
+            env.remove(PROXY_GIT_SSH_COMMAND_ENV_KEY);
+        }
+    }
+    env
+}
+
 /// POSIX-only helper: for commands produced by `Shell::derive_exec_args`
 /// for Bash/Zsh/sh of the form `[shell_path, "-lc", "<script>"]`, and
 /// when a snapshot is configured on the session shell, rewrite the argv
diff --git a/codex-rs/core/src/tools/runtimes/mod_tests.rs b/codex-rs/core/src/tools/runtimes/mod_tests.rs
index 0c9acd413..e4753533a 100644
--- a/codex-rs/core/src/tools/runtimes/mod_tests.rs
+++ b/codex-rs/core/src/tools/runtimes/mod_tests.rs
@@ -1,11 +1,29 @@
 use super::*;
+use crate::exec::ExecCapturePolicy;
+use crate::exec::ExecExpiration;
+use crate::sandboxing::ExecOptions;
 use crate::shell::ShellType;
 use crate::shell_snapshot::ShellSnapshot;
+use crate::tools::sandboxing::SandboxAttempt;
+use crate::tools::sandboxing::managed_network_for_sandbox_permissions;
 #[cfg(target_os = "macos")]
 use codex_network_proxy::CODEX_PROXY_GIT_SSH_COMMAND_MARKER;
+use codex_network_proxy::ConfigReloader;
+use codex_network_proxy::ConfigState;
+use codex_network_proxy::NetworkProxy;
+use codex_network_proxy::NetworkProxyConfig;
+use codex_network_proxy::NetworkProxyConstraints;
+use codex_network_proxy::NetworkProxyState;
 use codex_network_proxy::PROXY_ACTIVE_ENV_KEY;
+use codex_network_proxy::PROXY_ENV_KEYS;
 #[cfg(target_os = "macos")]
 use codex_network_proxy::PROXY_GIT_SSH_COMMAND_ENV_KEY;
+use codex_protocol::config_types::WindowsSandboxLevel;
+use codex_protocol::permissions::FileSystemSandboxPolicy;
+use codex_protocol::permissions::NetworkSandboxPolicy;
+use codex_protocol::protocol::SandboxPolicy;
+use codex_sandboxing::SandboxManager;
+use codex_sandboxing::SandboxType;
 use codex_utils_absolute_path::AbsolutePathBuf;
 use core_test_support::PathBufExt;
 use core_test_support::PathExt;
@@ -16,6 +34,23 @@ use std::sync::Arc;
 use tempfile::tempdir;
 use tokio::sync::watch;
 
+struct StaticReloader;
+
+#[async_trait::async_trait]
+impl ConfigReloader for StaticReloader {
+    fn source_label(&self) -> String {
+        "test config state".to_string()
+    }
+
+    async fn maybe_reload(&self) -> anyhow::Result<Option<ConfigState>> {
+        Ok(None)
+    }
+
+    async fn reload_now(&self) -> anyhow::Result<ConfigState> {
+        Err(anyhow::anyhow!("force reload is not supported in tests"))
+    }
+}
+
 fn shell_with_snapshot(
     shell_type: ShellType,
     shell_path: &str,
@@ -33,6 +68,104 @@ fn shell_with_snapshot(
     }
 }
 
+async fn test_network_proxy() -> anyhow::Result<NetworkProxy> {
+    let state = codex_network_proxy::build_config_state(
+        NetworkProxyConfig::default(),
+        NetworkProxyConstraints::default(),
+    )?;
+    NetworkProxy::builder()
+        .state(Arc::new(NetworkProxyState::with_reloader(
+            state,
+            Arc::new(StaticReloader),
+        )))
+        .managed_by_codex(/*managed_by_codex*/ false)
+        .http_addr("127.0.0.1:43128".parse()?)
+        .socks_addr("127.0.0.1:48081".parse()?)
+        .build()
+        .await
+}
+
+#[tokio::test]
+async fn explicit_escalation_prepares_exec_without_managed_network() -> anyhow::Result<()> {
+    let proxy = test_network_proxy().await?;
+    let dir = tempdir().expect("create temp dir");
+    let cwd = dir.path().abs();
+    let mut env = HashMap::from([("CUSTOM_ENV".to_string(), "kept".to_string())]);
+    proxy.apply_to_env(&mut env);
+
+    let command = vec!["/bin/echo".to_string(), "ok".to_string()];
+    let command = build_sandbox_command(
+        &command,
+        &cwd,
+        &exec_env_for_sandbox_permissions(&env, SandboxPermissions::RequireEscalated),
+        /*additional_permissions*/ None,
+    )
+    .expect("build sandbox command");
+    let options = ExecOptions {
+        expiration: ExecExpiration::DefaultTimeout,
+        capture_policy: ExecCapturePolicy::ShellTool,
+    };
+    let sandbox_policy = SandboxPolicy::DangerFullAccess;
+    let file_system_policy = FileSystemSandboxPolicy::from(&sandbox_policy);
+    let manager = SandboxManager::new();
+    let attempt = SandboxAttempt {
+        sandbox: SandboxType::None,
+        policy: &sandbox_policy,
+        file_system_policy: &file_system_policy,
+        network_policy: NetworkSandboxPolicy::Enabled,
+        enforce_managed_network: false,
+        manager: &manager,
+        sandbox_cwd: &cwd,
+        codex_linux_sandbox_exe: None,
+        use_legacy_landlock: false,
+        windows_sandbox_level: WindowsSandboxLevel::Disabled,
+        windows_sandbox_private_desktop: false,
+    };
+
+    let exec_request = attempt
+        .env_for(
+            command,
+            options,
+            managed_network_for_sandbox_permissions(
+                Some(&proxy),
+                SandboxPermissions::RequireEscalated,
+            ),
+        )
+        .expect("prepare exec request");
+
+    assert_eq!(exec_request.network, None);
+    for key in PROXY_ENV_KEYS {
+        assert_eq!(exec_request.env.get(*key), None, "{key} should be unset");
+    }
+    #[cfg(target_os = "macos")]
+    assert_eq!(exec_request.env.get(PROXY_GIT_SSH_COMMAND_ENV_KEY), None);
+    assert_eq!(
+        exec_request.env.get("CUSTOM_ENV"),
+        Some(&"kept".to_string())
+    );
+
+    Ok(())
+}
+
+#[test]
+fn explicit_escalation_keeps_user_proxy_env_without_codex_marker() {
+    let env = HashMap::from([
+        (
+            "HTTP_PROXY".to_string(),
+            "http://user.proxy:8080".to_string(),
+        ),
+        ("CUSTOM_ENV".to_string(), "kept".to_string()),
+    ]);
+
+    let env = exec_env_for_sandbox_permissions(&env, SandboxPermissions::RequireEscalated);
+
+    assert_eq!(
+        env.get("HTTP_PROXY"),
+        Some(&"http://user.proxy:8080".to_string())
+    );
+    assert_eq!(env.get("CUSTOM_ENV"), Some(&"kept".to_string()));
+}
+
 #[test]
 fn maybe_wrap_shell_lc_with_snapshot_bootstraps_in_user_shell() {
     let dir = tempdir().expect("create temp dir");
diff --git a/codex-rs/core/src/tools/runtimes/shell.rs b/codex-rs/core/src/tools/runtimes/shell.rs
index edaa2f472..b5e9c9805 100644
--- a/codex-rs/core/src/tools/runtimes/shell.rs
+++ b/codex-rs/core/src/tools/runtimes/shell.rs
@@ -20,6 +20,7 @@ use crate::shell::ShellType;
 use crate::tools::network_approval::NetworkApprovalMode;
 use crate::tools::network_approval::NetworkApprovalSpec;
 use crate::tools::runtimes::build_sandbox_command;
+use crate::tools::runtimes::exec_env_for_sandbox_permissions;
 use crate::tools::runtimes::maybe_wrap_shell_lc_with_snapshot;
 use crate::tools::sandboxing::Approvable;
 use crate::tools::sandboxing::ApprovalCtx;
@@ -31,6 +32,7 @@ use crate::tools::sandboxing::Sandboxable;
 use crate::tools::sandboxing::ToolCtx;
 use crate::tools::sandboxing::ToolError;
 use crate::tools::sandboxing::ToolRuntime;
+use crate::tools::sandboxing::managed_network_for_sandbox_permissions;
 use crate::tools::sandboxing::sandbox_override_for_first_attempt;
 use crate::tools::sandboxing::with_cached_approval;
 use codex_network_proxy::NetworkProxy;
@@ -218,9 +220,10 @@ impl ToolRuntime<ShellRequest, ExecToolCallOutput> for ShellRuntime {
         req: &ShellRequest,
         ctx: &ToolCtx,
     ) -> Option<NetworkApprovalSpec> {
-        req.network.as_ref()?;
+        let network =
+            managed_network_for_sandbox_permissions(req.network.as_ref(), req.sandbox_permissions)?;
         Some(NetworkApprovalSpec {
-            network: req.network.clone(),
+            network: Some(network.clone()),
             mode: NetworkApprovalMode::Immediate,
             trigger: GuardianNetworkAccessTrigger {
                 call_id: ctx.call_id.clone(),
@@ -243,12 +246,15 @@ impl ToolRuntime<ShellRequest, ExecToolCallOutput> for ShellRuntime {
         ctx: &ToolCtx,
     ) -> Result<ExecToolCallOutput, ToolError> {
         let session_shell = ctx.session.user_shell();
+        let managed_network =
+            managed_network_for_sandbox_permissions(req.network.as_ref(), req.sandbox_permissions);
+        let env = exec_env_for_sandbox_permissions(&req.env, req.sandbox_permissions);
         let command = maybe_wrap_shell_lc_with_snapshot(
             &req.command,
             session_shell.as_ref(),
             &req.cwd,
             &req.explicit_env_overrides,
-            &req.env,
+            &env,
         );
         let command = if matches!(session_shell.shell_type, ShellType::PowerShell) {
             prefix_powershell_script_with_utf8(&command)
@@ -267,18 +273,14 @@ impl ToolRuntime<ShellRequest, ExecToolCallOutput> for ShellRuntime {
             }
         }
 
-        let command = build_sandbox_command(
-            &command,
-            &req.cwd,
-            &req.env,
-            req.additional_permissions.clone(),
-        )?;
+        let command =
+            build_sandbox_command(&command, &req.cwd, &env, req.additional_permissions.clone())?;
         let options = ExecOptions {
             expiration: req.timeout_ms.into(),
             capture_policy: ExecCapturePolicy::ShellTool,
         };
         let env = attempt
-            .env_for(command, options, req.network.as_ref())
+            .env_for(command, options, managed_network)
             .map_err(|err| ToolError::Codex(err.into()))?;
         let out = execute_env(env, Self::stdout_stream(ctx))
             .await
diff --git a/codex-rs/core/src/tools/runtimes/shell/unix_escalation.rs b/codex-rs/core/src/tools/runtimes/shell/unix_escalation.rs
index 369689f9d..2484e914f 100644
--- a/codex-rs/core/src/tools/runtimes/shell/unix_escalation.rs
+++ b/codex-rs/core/src/tools/runtimes/shell/unix_escalation.rs
@@ -14,10 +14,12 @@ use crate::sandboxing::ExecRequest;
 use crate::sandboxing::SandboxPermissions;
 use crate::shell::ShellType;
 use crate::tools::runtimes::build_sandbox_command;
+use crate::tools::runtimes::exec_env_for_sandbox_permissions;
 use crate::tools::sandboxing::PermissionRequestPayload;
 use crate::tools::sandboxing::SandboxAttempt;
 use crate::tools::sandboxing::ToolCtx;
 use crate::tools::sandboxing::ToolError;
+use crate::tools::sandboxing::managed_network_for_sandbox_permissions;
 use codex_execpolicy::Decision;
 use codex_execpolicy::Evaluation;
 use codex_execpolicy::MatchOptions;
@@ -114,18 +116,19 @@ pub(super) async fn try_run_zsh_fork(
         return Ok(None);
     }
 
-    let command = build_sandbox_command(
-        command,
-        &req.cwd,
-        &req.env,
-        req.additional_permissions.clone(),
-    )?;
+    let env = exec_env_for_sandbox_permissions(&req.env, req.sandbox_permissions);
+    let command =
+        build_sandbox_command(command, &req.cwd, &env, req.additional_permissions.clone())?;
     let options = ExecOptions {
         expiration: req.timeout_ms.into(),
         capture_policy: ExecCapturePolicy::ShellTool,
     };
     let sandbox_exec_request = attempt
-        .env_for(command, options, req.network.as_ref())
+        .env_for(
+            command,
+            options,
+            managed_network_for_sandbox_permissions(req.network.as_ref(), req.sandbox_permissions),
+        )
         .map_err(|err| ToolError::Codex(err.into()))?;
     let crate::sandboxing::ExecRequest {
         command,
diff --git a/codex-rs/core/src/tools/runtimes/unified_exec.rs b/codex-rs/core/src/tools/runtimes/unified_exec.rs
index be185e5fe..f8ce24831 100644
--- a/codex-rs/core/src/tools/runtimes/unified_exec.rs
+++ b/codex-rs/core/src/tools/runtimes/unified_exec.rs
@@ -17,6 +17,7 @@ use crate::shell::ShellType;
 use crate::tools::network_approval::NetworkApprovalMode;
 use crate::tools::network_approval::NetworkApprovalSpec;
 use crate::tools::runtimes::build_sandbox_command;
+use crate::tools::runtimes::exec_env_for_sandbox_permissions;
 use crate::tools::runtimes::maybe_wrap_shell_lc_with_snapshot;
 use crate::tools::runtimes::shell::zsh_fork_backend;
 use crate::tools::sandboxing::Approvable;
@@ -29,6 +30,7 @@ use crate::tools::sandboxing::Sandboxable;
 use crate::tools::sandboxing::ToolCtx;
 use crate::tools::sandboxing::ToolError;
 use crate::tools::sandboxing::ToolRuntime;
+use crate::tools::sandboxing::managed_network_for_sandbox_permissions;
 use crate::tools::sandboxing::sandbox_override_for_first_attempt;
 use crate::tools::sandboxing::with_cached_approval;
 use crate::unified_exec::NoopSpawnLifecycle;
@@ -203,9 +205,10 @@ impl<'a> ToolRuntime<UnifiedExecRequest, UnifiedExecProcess> for UnifiedExecRunt
         req: &UnifiedExecRequest,
         ctx: &ToolCtx,
     ) -> Option<NetworkApprovalSpec> {
-        req.network.as_ref()?;
+        let network =
+            managed_network_for_sandbox_permissions(req.network.as_ref(), req.sandbox_permissions)?;
         Some(NetworkApprovalSpec {
-            network: req.network.clone(),
+            network: Some(network.clone()),
             mode: NetworkApprovalMode::Deferred,
             trigger: GuardianNetworkAccessTrigger {
                 call_id: ctx.call_id.clone(),
@@ -229,6 +232,12 @@ impl<'a> ToolRuntime<UnifiedExecRequest, UnifiedExecProcess> for UnifiedExecRunt
     ) -> Result<UnifiedExecProcess, ToolError> {
         let base_command = &req.command;
         let session_shell = ctx.session.user_shell();
+        let managed_network =
+            managed_network_for_sandbox_permissions(req.network.as_ref(), req.sandbox_permissions);
+        let mut env = exec_env_for_sandbox_permissions(&req.env, req.sandbox_permissions);
+        if let Some(network) = managed_network {
+            network.apply_to_env(&mut env);
+        }
         let environment_is_remote = ctx
             .turn
             .environment
@@ -242,7 +251,7 @@ impl<'a> ToolRuntime<UnifiedExecRequest, UnifiedExecProcess> for UnifiedExecRunt
                 session_shell.as_ref(),
                 &req.cwd,
                 &req.explicit_env_overrides,
-                &req.env,
+                &env,
             )
         };
         let command = if matches!(session_shell.shell_type, ShellType::PowerShell) {
@@ -251,10 +260,6 @@ impl<'a> ToolRuntime<UnifiedExecRequest, UnifiedExecProcess> for UnifiedExecRunt
             command
         };
 
-        let mut env = req.env.clone();
-        if let Some(network) = req.network.as_ref() {
-            network.apply_to_env(&mut env);
-        }
         if let UnifiedExecShellMode::ZshFork(zsh_fork_config) = &self.shell_mode {
             let command =
                 build_sandbox_command(&command, &req.cwd, &env, req.additional_permissions.clone())
@@ -264,7 +269,7 @@ impl<'a> ToolRuntime<UnifiedExecRequest, UnifiedExecProcess> for UnifiedExecRunt
                 capture_policy: ExecCapturePolicy::ShellTool,
             };
             let mut exec_env = attempt
-                .env_for(command, options, req.network.as_ref())
+                .env_for(command, options, managed_network)
                 .map_err(|err| ToolError::Codex(err.into()))?;
             exec_env.exec_server_env_config = req.exec_server_env_config.clone();
             match zsh_fork_backend::maybe_prepare_unified_exec(
@@ -322,7 +327,7 @@ impl<'a> ToolRuntime<UnifiedExecRequest, UnifiedExecProcess> for UnifiedExecRunt
             capture_policy: ExecCapturePolicy::ShellTool,
         };
         let mut exec_env = attempt
-            .env_for(command, options, req.network.as_ref())
+            .env_for(command, options, managed_network)
             .map_err(|err| ToolError::Codex(err.into()))?;
         exec_env.exec_server_env_config = req.exec_server_env_config.clone();
         let Some(environment) = ctx.turn.environment.as_ref() else {
diff --git a/codex-rs/core/src/tools/sandboxing.rs b/codex-rs/core/src/tools/sandboxing.rs
index 922ce6a1d..e8e17464a 100644
--- a/codex-rs/core/src/tools/sandboxing.rs
+++ b/codex-rs/core/src/tools/sandboxing.rs
@@ -265,6 +265,17 @@ pub(crate) fn sandbox_override_for_first_attempt(
     }
 }
 
+pub(crate) fn managed_network_for_sandbox_permissions(
+    network: Option<&NetworkProxy>,
+    sandbox_permissions: SandboxPermissions,
+) -> Option<&NetworkProxy> {
+    if sandbox_permissions.requires_escalated_permissions() {
+        None
+    } else {
+        network
+    }
+}
+
 pub(crate) trait Approvable<Req> {
     type ApprovalKey: Hash + Eq + Clone + Debug + Serialize;