diff --git a/e2e/framework/command.go b/e2e/framework/command.go
index 0d1955ed1..069c8eb33 100644
--- a/e2e/framework/command.go
+++ b/e2e/framework/command.go
@@ -145,7 +145,9 @@ func (f *Framework) DevsySSH(
 	workspace string,
 	command string,
 ) (string, error) {
-	out, err := f.ExecCommandOutput(ctx, []string{"ssh", workspace, "--command", command})
+	out, err := execWithSSHRetry(ctx, workspace, func(ctx context.Context) (string, error) {
+		return f.ExecCommandOutput(ctx, []string{"ssh", workspace, "--command", command})
+	})
 	if err != nil {
 		return "", fmt.Errorf("devsy ssh failed: %s", err.Error())
 	}
diff --git a/e2e/framework/retry.go b/e2e/framework/retry.go
index fa8141e1d..3b1d04fc5 100644
--- a/e2e/framework/retry.go
+++ b/e2e/framework/retry.go
@@ -4,6 +4,7 @@ import (
 	"context"
 	"errors"
 	"fmt"
+	"os/exec"
 	"strings"
 	"time"
 
@@ -20,6 +21,16 @@ var dockerPullBackoff = wait.Backoff{
 	Jitter:   0.1,
 }
 
+// sshBackoff defines retry timing for transient SSH failures on Windows+WSL
+// runners where the devsy agent binary injection can intermittently fail.
+// 3 total attempts (1 initial + 2 retries) with waits of ~5s, ~10s.
+var sshBackoff = wait.Backoff{
+	Steps:    3,
+	Duration: 5 * time.Second,
+	Factor:   2.0,
+	Jitter:   0.1,
+}
+
 // retryableDockerPatterns are stderr substrings indicating a transient Docker
 // registry error that is worth retrying.
 var retryableDockerPatterns = []string{
@@ -31,6 +42,17 @@ var retryableDockerPatterns = []string{
 	"503 Service Unavailable",
 }
 
+// isRetryableSSHError returns true when the error indicates a transient SSH
+// failure (exit code 1) typically caused by the devsy agent not yet being
+// ready inside the container.
+func isRetryableSSHError(err error) bool {
+	var exitErr *exec.ExitError
+	if errors.As(err, &exitErr) {
+		return exitErr.ExitCode() == 1
+	}
+	return false
+}
+
 // isRetryableDockerError returns true if stderr contains a transient Docker
 // registry error (rate limits, timeouts, connection resets).
 func isRetryableDockerError(stderr string) bool {
@@ -78,3 +100,41 @@ func execWithDockerRetry(
 	}
 	return lastStdout, lastStderr, err
 }
+
+// execWithSSHRetry runs fn and retries if the error indicates a transient SSH
+// failure (exit status 1). This handles the case where the devsy agent binary
+// injection into a WSL container has not completed yet.
+func execWithSSHRetry(
+	ctx context.Context,
+	workspace string,
+	fn func(ctx context.Context) (string, error),
+) (string, error) {
+	var lastOut string
+	var lastErr error
+	attempt := 0
+
+	err := wait.ExponentialBackoffWithContext(ctx, sshBackoff,
+		func(ctx context.Context) (bool, error) {
+			attempt++
+			lastOut, lastErr = fn(ctx)
+			if lastErr == nil {
+				return true, nil // success
+			}
+			if isRetryableSSHError(lastErr) {
+				ginkgo.GinkgoWriter.Printf(
+					"[retry] ssh %s: attempt %d failed with transient error, retrying: %s\n",
+					workspace, attempt, lastErr,
+				)
+				return false, nil // retry
+			}
+			return false, lastErr // non-retryable, stop immediately
+		},
+	)
+	if errors.Is(err, context.Canceled) || errors.Is(err, context.DeadlineExceeded) {
+		return lastOut, err
+	}
+	if err != nil && lastErr != nil {
+		return lastOut, fmt.Errorf("after %d attempts: %w", attempt, lastErr)
+	}
+	return lastOut, err
+}
diff --git a/e2e/framework/retry_test.go b/e2e/framework/retry_test.go
index 50fb59f46..3271a2b35 100644
--- a/e2e/framework/retry_test.go
+++ b/e2e/framework/retry_test.go
@@ -1,11 +1,46 @@
 package framework
 
 import (
+	"fmt"
+	"os/exec"
 	"testing"
 
 	"github.com/stretchr/testify/assert"
+	"github.com/stretchr/testify/require"
 )
 
+// exitError runs a shell command that exits with the given code and returns
+// the resulting *exec.ExitError.
+func exitError(t *testing.T, code string) *exec.ExitError {
+	t.Helper()
+	// #nosec G204 -- test helper with controlled exit code argument
+	err := exec.Command("sh", "-c", "exit "+code).Run()
+	require.Error(t, err)
+	var exitErr *exec.ExitError
+	require.ErrorAs(t, err, &exitErr)
+	return exitErr
+}
+
+func TestIsRetryableSSHError_ExitStatus1(t *testing.T) {
+	assert.True(t, isRetryableSSHError(exitError(t, "1")))
+}
+
+func TestIsRetryableSSHError_ExitStatus10(t *testing.T) {
+	assert.False(t, isRetryableSSHError(exitError(t, "10")))
+}
+
+func TestIsRetryableSSHError_ExitStatus127(t *testing.T) {
+	assert.False(t, isRetryableSSHError(exitError(t, "127")))
+}
+
+func TestIsRetryableSSHError_Nil(t *testing.T) {
+	assert.False(t, isRetryableSSHError(nil))
+}
+
+func TestIsRetryableSSHError_NonExitError(t *testing.T) {
+	assert.False(t, isRetryableSSHError(fmt.Errorf("some other error")))
+}
+
 func TestIsRetryableDockerError_RateLimit(t *testing.T) {
 	stderr := `GET https://index.docker.io/v2/library/ubuntu/manifests/latest: ` +
 		`TOOMANYREQUESTS: You have reached your unauthenticated pull rate limit.`