diff --git a/bin/periphery/src/api/build/mod.rs b/bin/periphery/src/api/build/mod.rs
index 021491b11..ff6ceaa47 100644
--- a/bin/periphery/src/api/build/mod.rs
+++ b/bin/periphery/src/api/build/mod.rs
@@ -271,7 +271,7 @@ impl Resolve<crate::api::Args> for build::Build {
         "Pre Build",
         pre_build_path.as_path(),
         &pre_build.command,
-        KomodoCommandMode::Multiline,
+        if pre_build.shell_mode { KomodoCommandMode::Shell } else { KomodoCommandMode::Multiline },
         &replacers,
       )
       .instrument(span)
diff --git a/bin/periphery/src/api/compose.rs b/bin/periphery/src/api/compose.rs
index 794067b25..22a218a3b 100644
--- a/bin/periphery/src/api/compose.rs
+++ b/bin/periphery/src/api/compose.rs
@@ -490,7 +490,7 @@ impl Resolve<crate::api::Args> for ComposeUp {
         "Pre Deploy",
         pre_deploy_path.as_path(),
         &stack.config.pre_deploy.command,
-        KomodoCommandMode::Multiline,
+        if stack.config.pre_deploy.shell_mode { KomodoCommandMode::Shell } else { KomodoCommandMode::Multiline },
         &replacers,
       )
       .instrument(span)
@@ -760,7 +760,7 @@ impl Resolve<crate::api::Args> for ComposeUp {
         "Post Deploy",
         post_deploy_path.as_path(),
         &stack.config.post_deploy.command,
-        KomodoCommandMode::Multiline,
+        if stack.config.post_deploy.shell_mode { KomodoCommandMode::Shell } else { KomodoCommandMode::Multiline },
         &replacers,
       )
       .instrument(span)
diff --git a/bin/periphery/src/helpers.rs b/bin/periphery/src/helpers.rs
index 623a4331c..4701134d1 100644
--- a/bin/periphery/src/helpers.rs
+++ b/bin/periphery/src/helpers.rs
@@ -189,7 +189,7 @@ pub async fn handle_post_repo_execution(
       "On Clone",
       path.as_path(),
       on_clone.command,
-      KomodoCommandMode::Multiline,
+      if on_clone.shell_mode { KomodoCommandMode::Shell } else { KomodoCommandMode::Multiline },
       &replacers,
     )
     .await
@@ -214,7 +214,7 @@ pub async fn handle_post_repo_execution(
       "On Pull",
       path.as_path(),
       on_pull.command,
-      KomodoCommandMode::Multiline,
+      if on_pull.shell_mode { KomodoCommandMode::Shell } else { KomodoCommandMode::Multiline },
       &replacers,
     )
     .await
diff --git a/client/core/rs/src/entities/mod.rs b/client/core/rs/src/entities/mod.rs
index cf5f817e0..9a9facf7a 100644
--- a/client/core/rs/src/entities/mod.rs
+++ b/client/core/rs/src/entities/mod.rs
@@ -215,6 +215,8 @@ pub struct SystemCommand {
   pub path: String,
   #[serde(default, deserialize_with = "file_contents_deserializer")]
   pub command: String,
+  #[serde(default)]
+  pub shell_mode: bool,
 }
 
 impl SystemCommand {
diff --git a/client/core/ts/src/types.ts b/client/core/ts/src/types.ts
index 4d4e0d186..7a78b3ed1 100644
--- a/client/core/ts/src/types.ts
+++ b/client/core/ts/src/types.ts
@@ -611,6 +611,7 @@ export interface ImageRegistryConfig {
 export interface SystemCommand {
 	path?: string;
 	command?: string;
+	shell_mode?: boolean;
 }
 
 /** The build configuration. */
diff --git a/ui/public/client/types.d.ts b/ui/public/client/types.d.ts
index 4374fb160..fbe2fa368 100644
--- a/ui/public/client/types.d.ts
+++ b/ui/public/client/types.d.ts
@@ -606,6 +606,7 @@ export interface ImageRegistryConfig {
 export interface SystemCommand {
     path?: string;
     command?: string;
+    shell_mode?: boolean;
 }
 /** The build configuration. */
 export interface BuildConfig {
diff --git a/ui/src/components/config/system-command.tsx b/ui/src/components/config/system-command.tsx
index b6ddfe2ee..bef3bfd4b 100644
--- a/ui/src/components/config/system-command.tsx
+++ b/ui/src/components/config/system-command.tsx
@@ -1,4 +1,4 @@
-import { Stack, TextInput } from "@mantine/core";
+import { Checkbox, Code, Stack, TextInput } from "@mantine/core";
 import { Types } from "komodo_client";
 import { MonacoEditor } from "@/components/monaco";
 
@@ -13,6 +13,9 @@ export default function SystemCommand({
   disabled,
   set,
 }: SystemCommandProps) {
+  const placeholder = value?.shell_mode
+    ? "  # Add a command to run.\n  "
+    : "  # Add multiple commands on new lines. Supports comments and escaped newlines.\n  ";
   return (
     <Stack>
       <TextInput
@@ -23,11 +26,27 @@ export default function SystemCommand({
         onChange={(e) => set({ ...(value || {}), path: e.target.value })}
         disabled={disabled}
       />
-      <MonacoEditor
-        value={
-          value?.command ||
-          "  # Add multiple commands on new lines. Supports comments.\n  "
+      <Checkbox
+        label={
+          <>
+            Run in shell mode (
+            <Code fz="sm" p="0">
+              sh -c
+            </Code>
+            ){" "}
+          </>
+        }
+        checked={value?.shell_mode ?? false}
+        onChange={(e) =>
+          set({
+            ...(value || {}),
+            shell_mode: e.currentTarget.checked,
+          })
         }
+        disabled={disabled}
+      />
+      <MonacoEditor
+        value={value?.command || placeholder}
         language="shell"
         onValueChange={(command) => set({ ...(value || {}), command })}
         readOnly={disabled}