diff --git a/web/server/entrypoint.go b/web/server/entrypoint.go
index 1656d89db23..69de5cc8ed8 100644
--- a/web/server/entrypoint.go
+++ b/web/server/entrypoint.go
@@ -25,6 +25,7 @@ import (
 	"go.viam.com/rdk/config"
 	"go.viam.com/rdk/logging"
 	"go.viam.com/rdk/resource"
+	"go.viam.com/rdk/robot"
 	robotimpl "go.viam.com/rdk/robot/impl"
 	"go.viam.com/rdk/robot/web"
 	weboptions "go.viam.com/rdk/robot/web/options"
@@ -249,6 +250,92 @@ func (s *robotServer) createWebOptions(cfg *config.Config) (weboptions.Options,
 	return options, nil
 }
 
+// A wrapper around actual config processing that also applies options from the
+// robot server.
+func (s *robotServer) processConfig(in *config.Config) (*config.Config, error) {
+	out, err := config.ProcessConfig(in)
+	if err != nil {
+		return nil, err
+	}
+	out.Debug = s.args.Debug || in.Debug
+	out.EnableWebProfile = s.args.WebProfile || in.EnableWebProfile
+	out.FromCommand = true
+	out.AllowInsecureCreds = s.args.AllowInsecureCreds
+	out.UntrustedEnv = s.args.UntrustedEnv
+	out.PackagePath = path.Join(viamDotDir, "packages")
+	return out, nil
+}
+
+// A function to be started as a goroutine that watches for changes, either
+// from disk or from cloud, to the robot's config. Starts comparisons based on
+// `currCfg`. Reconfigures the robot when config changes are received from the
+// watcher.
+func (s *robotServer) configWatcher(ctx context.Context, currCfg *config.Config, r robot.LocalRobot,
+	watcher config.Watcher,
+) {
+	// Reconfigure robot to have passed-in config before listening for any config
+	// changes.
+	r.Reconfigure(ctx, currCfg)
+
+	// Once reconfigure with initial config is complete; set initializing to
+	// false. Robot is now fully running and can indicate this through the
+	// MachineStatus endpoint.
+	r.SetInitializing(false)
+
+	for {
+		select {
+		case <-ctx.Done():
+			return
+		default:
+		}
+		select {
+		case <-ctx.Done():
+			return
+		case cfg := <-watcher.Config():
+			processedConfig, err := s.processConfig(cfg)
+			if err != nil {
+				s.logger.Errorw("reconfiguration aborted: error processing config", "error", err)
+				continue
+			}
+
+			// flag to restart web service if necessary
+			diff, err := config.DiffConfigs(*currCfg, *processedConfig, s.args.RevealSensitiveConfigDiffs)
+			if err != nil {
+				s.logger.Errorw("reconfiguration aborted: error diffing config", "error", err)
+				continue
+			}
+			var options weboptions.Options
+
+			if !diff.NetworkEqual {
+				// TODO(RSDK-2694): use internal web service reconfiguration instead
+				r.StopWeb()
+				options, err = s.createWebOptions(processedConfig)
+				if err != nil {
+					s.logger.Errorw("reconfiguration aborted: error creating weboptions", "error", err)
+					continue
+				}
+			}
+
+			// Update logger registry if log patterns may have changed.
+			//
+			// This functionality is tested in `TestLogPropagation` in `local_robot_test.go`.
+			if !diff.LogEqual {
+				s.logger.Debug("Detected potential changes to log patterns; updating logger levels")
+				config.UpdateLoggerRegistryFromConfig(s.registry, processedConfig, s.logger)
+			}
+
+			r.Reconfigure(ctx, processedConfig)
+
+			if !diff.NetworkEqual {
+				if err := r.StartWeb(ctx, options); err != nil {
+					s.logger.Errorw("reconfiguration failed: error starting web service while reconfiguring", "error", err)
+				}
+			}
+			currCfg = processedConfig
+		}
+	}
+}
+
 func (s *robotServer) serveWeb(ctx context.Context, cfg *config.Config) (err error) {
 	ctx, cancel := context.WithCancel(ctx)
 
@@ -324,21 +411,7 @@ func (s *robotServer) serveWeb(ctx context.Context, cfg *config.Config) (err err
 	defer cancel()
 	ctx = rpc.ContextWithDialer(ctx, rpcDialer)
 
-	processConfig := func(in *config.Config) (*config.Config, error) {
-		out, err := config.ProcessConfig(in)
-		if err != nil {
-			return nil, err
-		}
-		out.Debug = s.args.Debug || in.Debug
-		out.EnableWebProfile = s.args.WebProfile || in.EnableWebProfile
-		out.FromCommand = true
-		out.AllowInsecureCreds = s.args.AllowInsecureCreds
-		out.UntrustedEnv = s.args.UntrustedEnv
-		out.PackagePath = path.Join(viamDotDir, "packages")
-		return out, nil
-	}
-
-	fullProcessedConfig, err := processConfig(cfg)
+	fullProcessedConfig, err := s.processConfig(cfg)
 	if err != nil {
 		return err
 	}
@@ -434,80 +507,24 @@ func (s *robotServer) serveWeb(ctx context.Context, cfg *config.Config) (err err
 	defer func() {
 		err = multierr.Combine(err, watcher.Close())
 	}()
-	onWatchDone := make(chan struct{})
-	// Use `fullProcessedConfig` as the initial `oldCfg` for the config watcher
-	// goroutine, as we want incoming config changes to be compared to the full
-	// config.
-	oldCfg := fullProcessedConfig
-	utils.ManagedGo(func() {
-		// Reconfigure robot to have full processed config before listening for any
-		// config changes.
-		myRobot.Reconfigure(ctx, fullProcessedConfig)
-
-		// Once reconfigure with full processed config is complete; set initializing
-		// to false. Robot is now fully running and can indicate this through the
-		// MachineStatus endpoint.
-		myRobot.SetInitializing(false)
-
-		for {
-			select {
-			case <-ctx.Done():
-				return
-			default:
-			}
-			select {
-			case <-ctx.Done():
-				return
-			case cfg := <-watcher.Config():
-				processedConfig, err := processConfig(cfg)
-				if err != nil {
-					s.logger.Errorw("reconfiguration aborted: error processing config", "error", err)
-					continue
-				}
-
-				// flag to restart web service if necessary
-				diff, err := config.DiffConfigs(*oldCfg, *processedConfig, s.args.RevealSensitiveConfigDiffs)
-				if err != nil {
-					s.logger.Errorw("reconfiguration aborted: error diffing config", "error", err)
-					continue
-				}
-				var options weboptions.Options
-
-				if !diff.NetworkEqual {
-					// TODO(RSDK-2694): use internal web service reconfiguration instead
-					myRobot.StopWeb()
-					options, err = s.createWebOptions(processedConfig)
-					if err != nil {
-						s.logger.Errorw("reconfiguration aborted: error creating weboptions", "error", err)
-						continue
-					}
-				}
 
-				// Update logger registry if log patterns may have changed.
-				//
-				// This functionality is tested in `TestLogPropagation` in `local_robot_test.go`.
-				if !diff.LogEqual {
-					s.logger.Debug("Detected potential changes to log patterns; updating logger levels")
-					config.UpdateLoggerRegistryFromConfig(s.registry, processedConfig, s.logger)
-				}
-
-				myRobot.Reconfigure(ctx, processedConfig)
-
-				if !diff.NetworkEqual {
-					if err := myRobot.StartWeb(ctx, options); err != nil {
-						s.logger.Errorw("reconfiguration failed: error starting web service while reconfiguring", "error", err)
-					}
-				}
-				oldCfg = processedConfig
-			}
-		}
-	}, func() {
-		close(onWatchDone)
-	})
+	onWatchDone := make(chan struct{})
+	go func() {
+		defer func() {
+			close(onWatchDone)
+		}()
+
+		// Use `fullProcessedConfig` as the initial config for the config watcher
+		// goroutine, as we want incoming config changes to be compared to the full
+		// config.
+		s.configWatcher(ctx, fullProcessedConfig, myRobot, watcher)
+	}()
+	// At end of this function, cancel context and wait for watcher goroutine
+	// to complete.
 	defer func() {
+		cancel()
 		<-onWatchDone
 	}()
-	defer cancel()
 
 	// Create initial web options with `minimalProcessedConfig`.
 	options, err := s.createWebOptions(minimalProcessedConfig)