diff --git a/cmd/bbox/main.go b/cmd/bbox/main.go
index d1945be..1ba5092 100644
--- a/cmd/bbox/main.go
+++ b/cmd/bbox/main.go
@@ -871,9 +871,14 @@ func run(parentCtx context.Context, agentName string, flags runFlags) error {
 	}
 
 	if err != nil {
-		// Propagate the agent's exit code without printing an error.
+		// Propagate the agent's exit code.
 		var exitErr *infrassh.ExitError
 		if errors.As(err, &exitErr) {
+			// Print a diagnostic for unexpected terminations (OOM, crash, etc.)
+			// but stay quiet for normal exits and user-initiated signals.
+			if hint := exitErr.SignalHint(); hint != "" {
+				_, _ = fmt.Fprintf(os.Stderr, "\nSession ended unexpectedly: %s\n", hint)
+			}
 			// os.Exit bypasses defers, so clean up snapshot and flush
 			// the timing summary now.
 			if sb.Snapshot != nil {
diff --git a/internal/infra/ssh/terminal.go b/internal/infra/ssh/terminal.go
index cc18ddc..2c948bf 100644
--- a/internal/infra/ssh/terminal.go
+++ b/internal/infra/ssh/terminal.go
@@ -11,10 +11,12 @@ import (
 	"net"
 	"os"
 	"strings"
+	"syscall"
 	"time"
 
 	"golang.org/x/crypto/ssh"
 	"golang.org/x/crypto/ssh/agent"
+	"golang.org/x/sys/unix"
 
 	domainagent "github.com/stacklok/brood-box/pkg/domain/agent"
 	"github.com/stacklok/brood-box/pkg/domain/session"
@@ -46,13 +48,54 @@ func NewInteractiveSession(logger *slog.Logger) *InteractiveSession {
 
 // ExitError represents a non-zero exit code from the remote command.
 type ExitError struct {
-	Code int
+	Code   int
+	Signal string // SSH signal name (e.g. "KILL", "SEGV"), empty for normal exits
 }
 
 func (e *ExitError) Error() string {
+	if e.Signal != "" {
+		return fmt.Sprintf("remote command killed by signal SIG%s (exit code %d)", e.Signal, e.Code)
+	}
 	return fmt.Sprintf("remote command exited with code %d", e.Code)
 }
 
+// SignalHint returns a human-readable hint for unexpected terminations
+// (OOM kill, crash, etc.). Returns empty string for normal exits and
+// user-initiated signals (INT, TERM) which are expected.
+func (e *ExitError) SignalHint() string {
+	sigName := e.Signal
+	if sigName == "" {
+		// No SSH signal — check if exit code encodes one (128 + N convention).
+		sigName = signalNameFromCode(e.Code)
+	}
+	switch sigName {
+	case "KILL":
+		return "process was forcefully killed (likely out of memory — try increasing VM memory with --memory)"
+	case "SEGV":
+		return "process crashed with a segmentation fault"
+	case "ABRT":
+		return "process aborted (assertion failure or fatal error)"
+	default:
+		return ""
+	}
+}
+
+// signalNameFromCode returns the SSH-style signal name (e.g. "KILL") for an
+// exit code that follows the 128+N convention, or empty string if the code
+// does not encode a known signal.
+func signalNameFromCode(code int) string {
+	if code <= 128 {
+		return ""
+	}
+	sig := syscall.Signal(code - 128)
+	name := unix.SignalName(sig)
+	if name == "" {
+		return ""
+	}
+	// unix.SignalName returns "SIGKILL"; strip the "SIG" prefix.
+	return strings.TrimPrefix(name, "SIG")
+}
+
 // Run establishes an SSH connection, requests a PTY, and runs the command
 // interactively with full terminal forwarding.
 func (s *InteractiveSession) Run(ctx context.Context, opts session.SessionOpts) error {
@@ -167,7 +210,18 @@ func (s *InteractiveSession) Run(ctx context.Context, opts session.SessionOpts)
 	case err := <-done:
 		if err != nil {
 			if exitErr, ok := err.(*ssh.ExitError); ok {
-				return &ExitError{Code: exitErr.ExitStatus()}
+				code := exitErr.ExitStatus()
+				sig := exitErr.Signal()
+				// When killed by signal, SSH may report exit code 0 or -1.
+				// Use the conventional 128+N code instead.
+				if sig != "" && code <= 0 {
+					if n := unix.SignalNum("SIG" + sig); n > 0 {
+						code = 128 + int(n)
+					} else if code <= 0 {
+						code = 1
+					}
+				}
+				return &ExitError{Code: code, Signal: sig}
 			}
 			return fmt.Errorf("remote command failed: %w", err)
 		}
diff --git a/internal/infra/ssh/terminal_test.go b/internal/infra/ssh/terminal_test.go
index b8764be..5e0d56e 100644
--- a/internal/infra/ssh/terminal_test.go
+++ b/internal/infra/ssh/terminal_test.go
@@ -9,6 +9,68 @@ import (
 	"github.com/stretchr/testify/assert"
 )
 
+func TestExitError_SignalHint(t *testing.T) {
+	t.Parallel()
+
+	tests := []struct {
+		name     string
+		err      ExitError
+		expected string
+	}{
+		{
+			name:     "normal exit no hint",
+			err:      ExitError{Code: 1},
+			expected: "",
+		},
+		{
+			name:     "SIGKILL via signal field",
+			err:      ExitError{Code: 137, Signal: "KILL"},
+			expected: "process was forcefully killed (likely out of memory — try increasing VM memory with --memory)",
+		},
+		{
+			name:     "SIGKILL via exit code 137",
+			err:      ExitError{Code: 137},
+			expected: "process was forcefully killed (likely out of memory — try increasing VM memory with --memory)",
+		},
+		{
+			name:     "SIGSEGV via signal field",
+			err:      ExitError{Code: 139, Signal: "SEGV"},
+			expected: "process crashed with a segmentation fault",
+		},
+		{
+			name:     "SIGSEGV via exit code 139",
+			err:      ExitError{Code: 139},
+			expected: "process crashed with a segmentation fault",
+		},
+		{
+			name:     "SIGABRT via signal field",
+			err:      ExitError{Code: 134, Signal: "ABRT"},
+			expected: "process aborted (assertion failure or fatal error)",
+		},
+		{
+			name:     "SIGTERM is silent",
+			err:      ExitError{Code: 143, Signal: "TERM"},
+			expected: "",
+		},
+		{
+			name:     "SIGINT is silent",
+			err:      ExitError{Code: 130, Signal: "INT"},
+			expected: "",
+		},
+		{
+			name:     "exit code 143 without signal field is silent",
+			err:      ExitError{Code: 143},
+			expected: "",
+		},
+	}
+
+	for _, tt := range tests {
+		t.Run(tt.name, func(t *testing.T) {
+			assert.Equal(t, tt.expected, tt.err.SignalHint())
+		})
+	}
+}
+
 func TestBuildCommand_EscapesArgs(t *testing.T) {
 	t.Parallel()