diff --git a/blackbox/tasks_test.go b/blackbox/tasks_test.go
index c3f390e4b..3e54206b3 100644
--- a/blackbox/tasks_test.go
+++ b/blackbox/tasks_test.go
@@ -261,6 +261,29 @@ func TestRunPreservesArgumentBoundaries(t *testing.T) {
 	if !strings.Contains(r.Stdout, "hello   world") {
 		t.Fatalf("argument boundaries were lost; want \"hello   world\" in output, got:\n%s", r.Stdout)
 	}
+
+	r = m.MustRun("app", "run", "-a", name, "--", "printf '%s' 'hello world' | wc -c")
+	if strings.TrimSpace(r.Stdout) != "11" {
+		t.Fatalf("shell pipeline did not run; want 11, got:\n%s", r.Stdout)
+	}
+
+	r = m.MustRun("app", "run", "-a", name, "--", "expr", "3", ">", "2")
+	if strings.TrimSpace(r.Stdout) != "1" {
+		t.Fatalf("quoted comparison was interpreted as redirection; want 1, got:\n%s", r.Stdout)
+	}
+
+	r = m.MustRun("app", "run", "-a", name, "--", "echo $MIREN_APP")
+	if strings.TrimSpace(r.Stdout) != name {
+		t.Fatalf("shell variable did not expand; want %q, got:\n%s", name, r.Stdout)
+	}
+
+	r = m.MustRun("app", "run", "-a", name, "--", "printf 'redirected' > /tmp/miren-run-redirect; cat /tmp/miren-run-redirect")
+	if strings.TrimSpace(r.Stdout) != "redirected" {
+		t.Fatalf("shell redirection did not write a readable file; got:\n%s", r.Stdout)
+	}
+
+	r = m.Run("app", "run", "-a", name, "--", "exit 7")
+	r.RequireExitCode(t, 7)
 }
 
 // [tasks.<name>.env] has to reach the container. A task names no service, so
diff --git a/cli/commands/app_run.go b/cli/commands/app_run.go
index daed4fb7b..683790361 100644
--- a/cli/commands/app_run.go
+++ b/cli/commands/app_run.go
@@ -65,7 +65,7 @@ func AppRun(ctx *Context, opts struct {
 	// separate for whatever is reading them.
 	wantTTY := !opts.Detach && stdinIsTerminal()
 
-	created, err := runs.CreateRun(ctx, opts.App, opts.Task, opts.Args, wantTTY)
+	created, err := runs.CreateRun(ctx, opts.App, opts.Task, runCommand(opts.Args), wantTTY)
 	if err != nil {
 		return err
 	}
@@ -90,6 +90,17 @@ func AppRun(ctx *Context, opts struct {
 	return reportRunExit(ctx, runs, runID)
 }
 
+// runCommand treats a single command string as shell source. Multiple args
+// remain argv: the caller's shell already removed quoting, so even a standalone
+// operator token may be literal data deliberately quoted or escaped locally.
+func runCommand(args []string) []string {
+	const shellSyntax = "$|&;<>()`\\*?[]{}~\n"
+	if len(args) == 1 && strings.ContainsAny(args[0], shellSyntax+" \t") {
+		return []string{"/bin/sh", "-c", args[0]}
+	}
+	return args
+}
+
 // serverPredatesRuns reports whether a runsClient error means the cluster is
 // too old to offer durable runs, as opposed to being unreachable, wedged, or
 // refusing the caller.
diff --git a/cli/commands/app_run_doc.go b/cli/commands/app_run_doc.go
index f81ea67e0..268a8c8f9 100644
--- a/cli/commands/app_run_doc.go
+++ b/cli/commands/app_run_doc.go
@@ -4,6 +4,10 @@ const appRunDescription = `This command runs a command in a fresh sandbox built
 
 With no arguments it opens an interactive shell. With arguments it runs that command. With ` + "`" + `--task` + "`" + ` it runs a task declared in ` + "`" + `app.toml` + "`" + `.
 
+Pass a single command string to use shell syntax (such as ` + "`" + `$HOME` + "`" + `, ` + "`" + `|` + "`" + `, or ` + "`" + `>` + "`" + `). Multiple arguments retain their boundaries without shell interpretation, including quoted or escaped operator characters.
+
+Quote the expression for your local shell so it reaches Miren intact: ` + "`" + `miren app run -- 'echo $HOME | wc -c'` + "`" + `. Older clusters keep their existing command handling and may not interpret a single command string the same way.
+
 This is useful for:
 - Debugging application issues in an isolated environment
 - Running one-off commands with your app's configuration
diff --git a/cli/commands/app_run_test.go b/cli/commands/app_run_test.go
index 3de6bd659..80d0e0f22 100644
--- a/cli/commands/app_run_test.go
+++ b/cli/commands/app_run_test.go
@@ -2,6 +2,9 @@ package commands
 
 import (
 	"errors"
+	"os/exec"
+	"reflect"
+	"strings"
 	"testing"
 	"time"
 
@@ -11,6 +14,90 @@ import (
 	"miren.dev/runtime/pkg/ui"
 )
 
+func TestRunCommand(t *testing.T) {
+	tests := []struct {
+		name string
+		args []string
+		want []string
+	}{
+		{"console", nil, nil},
+		{"single executable", []string{"date"}, []string{"date"}},
+		{"ordinary arguments", []string{"echo", "hello   world", "O'Reilly"}, []string{"echo", "hello   world", "O'Reilly"}},
+		{"variable argument stays literal", []string{"echo", "$HOME"}, []string{"echo", "$HOME"}},
+		{"operator argument stays literal", []string{"grep", "-F", "|", "log"}, []string{"grep", "-F", "|", "log"}},
+		{"find exec terminator", []string{"find", ".", "-name", "x", "-exec", "rm", "{}", ";"}, []string{"find", ".", "-name", "x", "-exec", "rm", "{}", ";"}},
+		{"expr comparison", []string{"expr", "3", ">", "2"}, []string{"expr", "3", ">", "2"}},
+		{"single shell expression", []string{"echo $HOME | wc -c"}, []string{"/bin/sh", "-c", "echo $HOME | wc -c"}},
+		{"single command string", []string{"exit 7"}, []string{"/bin/sh", "-c", "exit 7"}},
+		{"redirect is data", []string{"echo", "hi", ">", "/tmp/result"}, []string{"echo", "hi", ">", "/tmp/result"}},
+		{"python code is data", []string{"python", "-c", "print('hi')"}, []string{"python", "-c", "print('hi')"}},
+		{"SQL is data", []string{"psql", "-c", "SELECT * FROM users;"}, []string{"psql", "-c", "SELECT * FROM users;"}},
+		{"URL is data", []string{"curl", "https://x/?a=1&b=2"}, []string{"curl", "https://x/?a=1&b=2"}},
+		{"grep pattern is data", []string{"grep", "-E", "foo|bar", "log"}, []string{"grep", "-E", "foo|bar", "log"}},
+		{"substitution is data", []string{"echo", "it's $HOME"}, []string{"echo", "it's $HOME"}},
+		{"explicit shell", []string{"/bin/sh", "-c", "echo $HOME | wc -c"}, []string{"/bin/sh", "-c", "echo $HOME | wc -c"}},
+		{"combined shell flags", []string{"sh", "-ec", "exit 7; echo unexpected"}, []string{"sh", "-ec", "exit 7; echo unexpected"}},
+		{"shell option value", []string{"sh", "-o", "pipefail", "-c", "echo 'x' | cat"}, []string{"sh", "-o", "pipefail", "-c", "echo 'x' | cat"}},
+		{"env shell", []string{"/usr/bin/env", "bash", "-c", "echo $HOME"}, []string{"/usr/bin/env", "bash", "-c", "echo $HOME"}},
+		{"login shell flags", []string{"bash", "-lc", "echo $1", "unused", "word"}, []string{"bash", "-lc", "echo $1", "unused", "word"}},
+		{"separate shell flags", []string{"bash", "-e", "-c", "echo $1", "unused", "word"}, []string{"bash", "-e", "-c", "echo $1", "unused", "word"}},
+	}
+	for _, tt := range tests {
+		t.Run(tt.name, func(t *testing.T) {
+			if got := runCommand(tt.args); !reflect.DeepEqual(got, tt.want) {
+				t.Fatalf("runCommand(%q) = %q, want %q", tt.args, got, tt.want)
+			}
+		})
+	}
+}
+
+func TestRunCommandExecutesShellExpression(t *testing.T) {
+	args := runCommand([]string{`printf '%s' 'hello world' | wc -c`})
+	out, err := exec.Command(args[0], args[1:]...).Output()
+	if err != nil {
+		t.Fatal(err)
+	}
+	if got := strings.TrimSpace(string(out)); got != "11" {
+		t.Fatalf("pipeline output = %q, want 11", got)
+	}
+}
+
+func TestRunCommandPreservesLiteralArguments(t *testing.T) {
+	for _, literal := range []string{"O'Reilly book", "a # b", "a = b", ""} {
+		t.Run(literal, func(t *testing.T) {
+			args := runCommand([]string{"printf", "%s", literal})
+			out, err := exec.Command(args[0], args[1:]...).Output()
+			if err != nil {
+				t.Fatal(err)
+			}
+			if string(out) != literal {
+				t.Fatalf("command output = %q, want %q", out, literal)
+			}
+		})
+	}
+}
+
+func TestRunCommandPreservesExplicitShellExit(t *testing.T) {
+	for _, args := range [][]string{
+		{"sh", "-ec", "exit 7; echo unexpected"},
+		{"bash", "-lc", "exit 7; echo unexpected"},
+		{"bash", "-e", "-c", "exit 7; echo unexpected"},
+	} {
+		got := runCommand(args)
+		out, err := exec.Command(got[0], got[1:]...).CombinedOutput()
+		var exit *exec.ExitError
+		if !errors.As(err, &exit) || exit.ExitCode() != 7 || len(out) != 0 {
+			t.Fatalf("%q: exit = %v, output = %q; want code 7 and no output", args, err, out)
+		}
+	}
+
+	args := runCommand([]string{"bash", "-lc", `printf '%s' "$1"`, "unused", "two words"})
+	out, err := exec.Command(args[0], args[1:]...).Output()
+	if err != nil || string(out) != "two words" {
+		t.Fatalf("positional argument output = %q, error = %v; want two words", out, err)
+	}
+}
+
 // The compatibility fallback hinges on one distinction: a server that answered
 // and does not offer app-runs (fall back to legacy exec) versus a server that
 // is unreachable, wedged, or refusing us (surface the real error). Falling back
diff --git a/docs/docs/command/app-run.md b/docs/docs/command/app-run.md
index 1d915718d..c6e99ef8d 100644
--- a/docs/docs/command/app-run.md
+++ b/docs/docs/command/app-run.md
@@ -12,6 +12,10 @@ This command runs a command in a fresh sandbox built from your app's active vers
 
 With no arguments it opens an interactive shell. With arguments it runs that command. With `--task` it runs a task declared in `app.toml`.
 
+Pass a single command string to use shell syntax (such as `$HOME`, `|`, or `>`). Multiple arguments retain their boundaries without shell interpretation, including quoted or escaped operator characters.
+
+Quote the expression for your local shell so it reaches Miren intact: `miren app run -- 'echo $HOME | wc -c'`. Older clusters keep their existing command handling and may not interpret a single command string the same way.
+
 This is useful for:
 - Debugging application issues in an isolated environment
 - Running one-off commands with your app's configuration