diff --git a/pkg/agent/delivery/remote_docker.go b/pkg/agent/delivery/remote_docker.go
index cb309622c..b646bf068 100644
--- a/pkg/agent/delivery/remote_docker.go
+++ b/pkg/agent/delivery/remote_docker.go
@@ -6,6 +6,7 @@ import (
 	"io"
 	"os"
 	"os/exec"
+	"path"
 
 	"github.com/devsy-org/devsy/pkg/agent"
 	"github.com/devsy-org/devsy/pkg/log"
@@ -40,6 +41,10 @@ func (d *RemoteDockerDelivery) DeliverPostStart(ctx context.Context, opts PostSt
 
 	destPath := agent.ContainerDevsyHelperLocation
 
+	if err := d.ensureDir(ctx, destPath); err != nil {
+		return fmt.Errorf("ensure target directory: %w", err)
+	}
+
 	if err := d.copyBinaryFromSource(ctx, opts.BinarySource, opts.Arch, destPath); err != nil {
 		return fmt.Errorf("copy binary to container: %w", err)
 	}
@@ -98,6 +103,15 @@ func (d *RemoteDockerDelivery) chmodBinary(ctx context.Context, destPath string)
 	return nil
 }
 
+func (d *RemoteDockerDelivery) ensureDir(ctx context.Context, filePath string) error {
+	dir := path.Dir(filePath)
+	out, err := d.cmd(ctx, "exec", d.ContainerID, "mkdir", "-p", dir).CombinedOutput()
+	if err != nil {
+		return fmt.Errorf("%s: %w", string(out), err)
+	}
+	return nil
+}
+
 func (d *RemoteDockerDelivery) cmd(ctx context.Context, args ...string) *exec.Cmd {
 	// #nosec G204 -- args are constructed internally, not from user input
 	cmd := exec.CommandContext(ctx, d.dockerCommand(), args...)