diff --git a/go/cmd/entrypoint/daemon_util.go b/go/cmd/entrypoint/daemon_util.go
index 566abe6..3e933a0 100644
--- a/go/cmd/entrypoint/daemon_util.go
+++ b/go/cmd/entrypoint/daemon_util.go
@@ -4,6 +4,7 @@ import (
 	"context"
 	"errors"
 	"fmt"
+	"io/fs"
 	"isle/daemon"
 	"isle/daemon/jsonrpc2"
 	"net"
@@ -22,11 +23,20 @@ func newHTTPServer(
 	*http.Server, error,
 ) {
 	socketPath := daemon.HTTPSocketPath()
+	ctx = mctx.Annotate(ctx, "socketPath", socketPath)
+
+	if err := os.Remove(socketPath); errors.Is(err, fs.ErrNotExist) {
+		// No problem
+	} else if err != nil {
+		return nil, fmt.Errorf(
+			"removing %q prior to listening: %w", socketPath, err,
+		)
+	} else {
+		logger.WarnString(
+			ctx, "Deleted existing socket file prior to listening, it's possible a previous daemon failed to shutdown gracefully",
+		)
+	}
 
-	// TODO I restarted isle once and when it came back up it errored here
-	// because the socket file already existed. isle should delete the file
-	// during shutdown, but it should also check if the file exists on startup
-	// in case shutdown wasn't clean.
 	l, err := net.Listen("unix", socketPath)
 	if err != nil {
 		return nil, fmt.Errorf(
@@ -40,7 +50,6 @@ func newHTTPServer(
 		)
 	}
 
-	ctx = mctx.Annotate(ctx, "httpAddr", l.Addr().String())
 	logger.Info(ctx, "HTTP server socket created")
 
 	rpcHandler := jsonrpc2.Chain(