diff --git a/internal/tools/credentialed_exec.go b/internal/tools/credentialed_exec.go
index 2ab9a52a..7fb78657 100644
--- a/internal/tools/credentialed_exec.go
+++ b/internal/tools/credentialed_exec.go
@@ -112,7 +112,11 @@ func (t *ExecTool) executeCredentialed(ctx context.Context, cred *store.SecureCL
 	// Step 2: Resolve binary to absolute path and verify against config
 	absPath, err := resolveAndMatchBinary(binary, cred.BinaryPath)
 	if err != nil {
-		return credentialedPathError(binary, err)
+		r := credentialedPathError(binary, err)
+		if t.sandboxMgr != nil && sandboxKey != "" {
+			r.ForLLM += sandboxHint
+		}
+		return r
 	}
 
 	// Step 3: Per-binary deny check (deny_args)
@@ -199,7 +203,8 @@ func (t *ExecTool) executeCredentialedSandbox(ctx context.Context, absPath strin
 		output += "STDERR:\n" + result.Stderr
 	}
 	if result.ExitCode != 0 {
-		return credentialedExecFailError(absPath, args, result.ExitCode, ScrubCredentials(output))
+		scrubbed := ScrubCredentials(output)
+		return credentialedExecFailError(absPath, args, result.ExitCode, scrubbed+MaybeSandboxHint(result.ExitCode, scrubbed))
 	}
 	if output == "" {
 		output = "(command completed with no output)"
diff --git a/internal/tools/sandbox_hints.go b/internal/tools/sandbox_hints.go
new file mode 100644
index 00000000..51b81256
--- /dev/null
+++ b/internal/tools/sandbox_hints.go
@@ -0,0 +1,32 @@
+package tools
+
+import "strings"
+
+// sandboxHint is appended to tool error output when a command fails inside
+// a Docker sandbox container due to a missing binary/tool (exit code 127).
+const sandboxHint = "\n\n[SANDBOX] This command ran inside a Docker sandbox container. " +
+	"The required tool/binary is not installed in the sandbox image. " +
+	"Tell the user this failed due to sandbox environment limitations — " +
+	"they can install the binary in the sandbox image or disable sandbox mode for this agent."
+
+// isBinaryNotFound returns true if the error output and exit code indicate
+// a missing binary. Exit code 127 is the POSIX convention for "command not found".
+func isBinaryNotFound(exitCode int, output string) bool {
+	if exitCode == 127 {
+		return true
+	}
+	// Fallback: match stderr patterns from non-standard shells.
+	lower := strings.ToLower(output)
+	return strings.Contains(lower, "not found") &&
+		(strings.Contains(lower, "command") || strings.Contains(lower, "sh:"))
+}
+
+// MaybeSandboxHint returns the sandbox hint suffix if the error looks like
+// a missing binary. Returns empty string otherwise.
+// Only call this from sandbox execution paths — never from host execution.
+func MaybeSandboxHint(exitCode int, output string) string {
+	if isBinaryNotFound(exitCode, output) {
+		return sandboxHint
+	}
+	return ""
+}
diff --git a/internal/tools/sandbox_hints_test.go b/internal/tools/sandbox_hints_test.go
new file mode 100644
index 00000000..711fb0aa
--- /dev/null
+++ b/internal/tools/sandbox_hints_test.go
@@ -0,0 +1,63 @@
+package tools
+
+import (
+	"strings"
+	"testing"
+)
+
+func TestIsBinaryNotFound(t *testing.T) {
+	tests := []struct {
+		name     string
+		exitCode int
+		output   string
+		want     bool
+	}{
+		{"exit 127 empty output", 127, "", true},
+		{"exit 127 with sh not found", 127, "sh: git: not found", true},
+		{"exit 127 with bash error", 127, "bash: python3: command not found", true},
+		{"exit 1 permission denied", 1, "permission denied", false},
+		{"exit 0 success", 0, "ok", false},
+		{"exit 1 sh not found pattern", 1, "sh: node: not found", true},
+		{"exit 1 command not found pattern", 1, "bash: command not found: curl", true},
+		{"exit 1 unrelated not found", 1, "file not found: config.yaml", false},
+		{"exit 2 no such file", 2, "No such file or directory", false},
+	}
+
+	for _, tt := range tests {
+		t.Run(tt.name, func(t *testing.T) {
+			got := isBinaryNotFound(tt.exitCode, tt.output)
+			if got != tt.want {
+				t.Errorf("isBinaryNotFound(%d, %q) = %v, want %v", tt.exitCode, tt.output, got, tt.want)
+			}
+		})
+	}
+}
+
+func TestMaybeSandboxHint(t *testing.T) {
+	tests := []struct {
+		name      string
+		exitCode  int
+		output    string
+		wantHint  bool
+	}{
+		{"binary not found returns hint", 127, "sh: git: not found", true},
+		{"success returns empty", 0, "ok", false},
+		{"non-binary error returns empty", 1, "segfault", false},
+		{"sh pattern returns hint", 1, "sh: python3: not found", true},
+	}
+
+	for _, tt := range tests {
+		t.Run(tt.name, func(t *testing.T) {
+			got := MaybeSandboxHint(tt.exitCode, tt.output)
+			if tt.wantHint {
+				if !strings.Contains(got, "[SANDBOX]") {
+					t.Errorf("MaybeSandboxHint(%d, %q) = %q, want hint containing [SANDBOX]", tt.exitCode, tt.output, got)
+				}
+			} else {
+				if got != "" {
+					t.Errorf("MaybeSandboxHint(%d, %q) = %q, want empty", tt.exitCode, tt.output, got)
+				}
+			}
+		})
+	}
+}
diff --git a/internal/tools/shell.go b/internal/tools/shell.go
index b61eb757..f31dad44 100644
--- a/internal/tools/shell.go
+++ b/internal/tools/shell.go
@@ -322,6 +322,7 @@ func (t *ExecTool) executeInSandbox(ctx context.Context, command, cwd, sandboxKe
 		if output == "" {
 			output = fmt.Sprintf("command exited with code %d", result.ExitCode)
 		}
+		output += MaybeSandboxHint(result.ExitCode, output)
 		return ErrorResult(output)
 	}
 	if output == "" {