diff --git a/cmd/cli/cli.go b/cmd/cli/cli.go
index 06dffcb..b0c03c3 100644
--- a/cmd/cli/cli.go
+++ b/cmd/cli/cli.go
@@ -761,6 +761,8 @@ func processListenFlag() {
 	if listenAddress == "" {
 		return
 	}
+	mainLog.Load().Debug().Str("listen_address", listenAddress).Msg("Processing listen flag")
+
 	host, portStr, err := net.SplitHostPort(listenAddress)
 	if err != nil {
 		mainLog.Load().Fatal().Msgf("invalid listener address: %v", err)
@@ -776,22 +778,31 @@ func processListenFlag() {
 	v.Set("listener", map[string]*ctrld.ListenerConfig{
 		"0": lc,
 	})
+
+	mainLog.Load().Debug().Str("host", host).Int("port", port).Msg("Listen flag processed successfully")
 }
 
 // processLogAndCacheFlags processes log and cache related flags
 func processLogAndCacheFlags() {
+	mainLog.Load().Debug().Msg("Processing log and cache flags")
+
 	if logPath != "" {
 		cfg.Service.LogPath = logPath
+		mainLog.Load().Debug().Str("log_path", logPath).Msg("Log path flag processed")
 	}
 	if logPath != "" && cfg.Service.LogLevel == "" {
 		cfg.Service.LogLevel = "debug"
+		mainLog.Load().Debug().Msg("Log level set to debug")
 	}
 
 	if cacheSize != 0 {
 		cfg.Service.CacheEnable = true
 		cfg.Service.CacheSize = cacheSize
+		mainLog.Load().Debug().Int("cache_size", cacheSize).Msg("Cache flag processed")
 	}
 	v.Set("service", cfg.Service)
+
+	mainLog.Load().Debug().Msg("Log and cache flags processed successfully")
 }
 
 // netInterface returns the network interface by name
@@ -1075,6 +1086,8 @@ func uninstall(p *prog, s service.Service) {
 }
 
 func validateConfig(cfg *ctrld.Config) error {
+	mainLog.Load().Debug().Msg("Validating configuration")
+
 	if err := ctrld.ValidateConfig(validator.New(), cfg); err != nil {
 		var ve validator.ValidationErrors
 		if errors.As(err, &ve) {
@@ -1082,8 +1095,11 @@ func validateConfig(cfg *ctrld.Config) error {
 				mainLog.Load().Error().Msgf("invalid config: %s: %s", fe.Namespace(), fieldErrorMsg(fe))
 			}
 		}
+		mainLog.Load().Error().Err(err).Msg("Configuration validation failed")
 		return err
 	}
+
+	mainLog.Load().Debug().Msg("Configuration validation completed successfully")
 	return nil
 }
 
diff --git a/cmd/cli/os_darwin.go b/cmd/cli/os_darwin.go
index 68bd7e1..94e45fd 100644
--- a/cmd/cli/os_darwin.go
+++ b/cmd/cli/os_darwin.go
@@ -14,21 +14,25 @@ import (
 // allocateIP allocates an IP address on the specified interface
 // sudo ifconfig lo0 alias 127.0.0.2 up
 func allocateIP(ip string) error {
+	mainLog.Load().Debug().Str("ip", ip).Msg("Allocating IP address")
 	cmd := exec.Command("ifconfig", "lo0", "alias", ip, "up")
 	if err := cmd.Run(); err != nil {
 		mainLog.Load().Error().Err(err).Msg("allocateIP failed")
 		return err
 	}
+	mainLog.Load().Debug().Str("ip", ip).Msg("IP address allocated successfully")
 	return nil
 }
 
 // deAllocateIP deallocates an IP address from the specified interface
 func deAllocateIP(ip string) error {
+	mainLog.Load().Debug().Str("ip", ip).Msg("Deallocating IP address")
 	cmd := exec.Command("ifconfig", "lo0", "-alias", ip)
 	if err := cmd.Run(); err != nil {
 		mainLog.Load().Error().Err(err).Msg("deAllocateIP failed")
 		return err
 	}
+	mainLog.Load().Debug().Str("ip", ip).Msg("IP address deallocated successfully")
 	return nil
 }
 
@@ -48,6 +52,8 @@ func setDnsIgnoreUnusableInterface(iface *net.Interface, nameservers []string) e
 // networksetup -setdnsservers Wi-Fi 8.8.8.8 1.1.1.1
 // TODO(cuonglm): use system API
 func setDNS(iface *net.Interface, nameservers []string) error {
+	mainLog.Load().Debug().Str("interface", iface.Name).Strs("nameservers", nameservers).Msg("Setting DNS configuration")
+
 	// Note that networksetup won't modify search domains settings,
 	// This assignment is just a placeholder to silent linter.
 	_ = searchDomains
@@ -57,6 +63,8 @@ func setDNS(iface *net.Interface, nameservers []string) error {
 	if out, err := exec.Command(cmd, args...).CombinedOutput(); err != nil {
 		return fmt.Errorf("%v: %w", string(out), err)
 	}
+
+	mainLog.Load().Debug().Str("interface", iface.Name).Msg("DNS configuration set successfully")
 	return nil
 }
 
@@ -74,11 +82,15 @@ func resetDnsIgnoreUnusableInterface(iface *net.Interface) error {
 
 // TODO(cuonglm): use system API
 func resetDNS(iface *net.Interface) error {
+	mainLog.Load().Debug().Str("interface", iface.Name).Msg("Resetting DNS configuration")
+
 	cmd := "networksetup"
 	args := []string{"-setdnsservers", iface.Name, "empty"}
 	if out, err := exec.Command(cmd, args...).CombinedOutput(); err != nil {
 		return fmt.Errorf("%v: %w", string(out), err)
 	}
+
+	mainLog.Load().Debug().Str("interface", iface.Name).Msg("DNS configuration reset successfully")
 	return nil
 }
 
diff --git a/cmd/cli/os_freebsd.go b/cmd/cli/os_freebsd.go
index 65c44b9..9a7777d 100644
--- a/cmd/cli/os_freebsd.go
+++ b/cmd/cli/os_freebsd.go
@@ -16,21 +16,25 @@ import (
 // allocateIP allocates an IP address on the specified interface
 // sudo ifconfig lo0 127.0.0.53 alias
 func allocateIP(ip string) error {
+	mainLog.Load().Debug().Str("ip", ip).Msg("Allocating IP address")
 	cmd := exec.Command("ifconfig", "lo0", ip, "alias")
 	if err := cmd.Run(); err != nil {
 		mainLog.Load().Error().Err(err).Msg("allocateIP failed")
 		return err
 	}
+	mainLog.Load().Debug().Str("ip", ip).Msg("IP address allocated successfully")
 	return nil
 }
 
 // deAllocateIP deallocates an IP address from the specified interface
 func deAllocateIP(ip string) error {
+	mainLog.Load().Debug().Str("ip", ip).Msg("Deallocating IP address")
 	cmd := exec.Command("ifconfig", "lo0", ip, "-alias")
 	if err := cmd.Run(); err != nil {
 		mainLog.Load().Error().Err(err).Msg("deAllocateIP failed")
 		return err
 	}
+	mainLog.Load().Debug().Str("ip", ip).Msg("IP address deallocated successfully")
 	return nil
 }
 
@@ -41,6 +45,8 @@ func setDnsIgnoreUnusableInterface(iface *net.Interface, nameservers []string) e
 
 // set the dns server for the provided network interface
 func setDNS(iface *net.Interface, nameservers []string) error {
+	mainLog.Load().Debug().Str("interface", iface.Name).Strs("nameservers", nameservers).Msg("Setting DNS configuration")
+
 	r, err := dns.NewOSConfigurator(logf, &health.Tracker{}, &controlknobs.Knobs{}, iface.Name)
 	if err != nil {
 		mainLog.Load().Error().Err(err).Msg("failed to create DNS OS configurator")
@@ -66,6 +72,8 @@ func setDNS(iface *net.Interface, nameservers []string) error {
 		mainLog.Load().Error().Err(err).Msg("failed to set DNS")
 		return err
 	}
+
+	mainLog.Load().Debug().Str("interface", iface.Name).Msg("DNS configuration set successfully")
 	return nil
 }
 
@@ -76,6 +84,8 @@ func resetDnsIgnoreUnusableInterface(iface *net.Interface) error {
 
 // resetDNS resets DNS servers for the specified interface
 func resetDNS(iface *net.Interface) error {
+	mainLog.Load().Debug().Str("interface", iface.Name).Msg("Resetting DNS configuration")
+
 	r, err := dns.NewOSConfigurator(logf, &health.Tracker{}, &controlknobs.Knobs{}, iface.Name)
 	if err != nil {
 		mainLog.Load().Error().Err(err).Msg("failed to create DNS OS configurator")
@@ -86,6 +96,8 @@ func resetDNS(iface *net.Interface) error {
 		mainLog.Load().Error().Err(err).Msg("failed to rollback DNS setting")
 		return err
 	}
+
+	mainLog.Load().Debug().Str("interface", iface.Name).Msg("DNS configuration reset successfully")
 	return nil
 }
 
diff --git a/cmd/cli/os_linux.go b/cmd/cli/os_linux.go
index 0b93b0b..b4fef82 100644
--- a/cmd/cli/os_linux.go
+++ b/cmd/cli/os_linux.go
@@ -33,20 +33,24 @@ type getDNS func(iface string) []string
 // allocate loopback ip
 // sudo ip a add 127.0.0.2/24 dev lo
 func allocateIP(ip string) error {
+	mainLog.Load().Debug().Str("ip", ip).Msg("Allocating IP address")
 	cmd := exec.Command("ip", "a", "add", ip+"/24", "dev", "lo")
 	if out, err := cmd.CombinedOutput(); err != nil {
 		mainLog.Load().Error().Err(err).Msgf("allocateIP failed: %s", string(out))
 		return err
 	}
+	mainLog.Load().Debug().Str("ip", ip).Msg("IP address allocated successfully")
 	return nil
 }
 
 func deAllocateIP(ip string) error {
+	mainLog.Load().Debug().Str("ip", ip).Msg("Deallocating IP address")
 	cmd := exec.Command("ip", "a", "del", ip+"/24", "dev", "lo")
 	if err := cmd.Run(); err != nil {
 		mainLog.Load().Error().Err(err).Msg("deAllocateIP failed")
 		return err
 	}
+	mainLog.Load().Debug().Str("ip", ip).Msg("IP address deallocated successfully")
 	return nil
 }
 
@@ -58,6 +62,8 @@ func setDnsIgnoreUnusableInterface(iface *net.Interface, nameservers []string) e
 }
 
 func setDNS(iface *net.Interface, nameservers []string) error {
+	mainLog.Load().Debug().Str("interface", iface.Name).Strs("nameservers", nameservers).Msg("Setting DNS configuration")
+
 	r, err := dns.NewOSConfigurator(logf, &health.Tracker{}, &controlknobs.Knobs{}, iface.Name)
 	if err != nil {
 		mainLog.Load().Error().Err(err).Msg("failed to create DNS OS configurator")
@@ -119,6 +125,8 @@ systemdResolve:
 		}
 		mainLog.Load().Debug().Msg("DNS was not set for some reason")
 	}
+
+	mainLog.Load().Debug().Str("interface", iface.Name).Msg("DNS configuration set successfully")
 	return nil
 }
 
@@ -128,6 +136,8 @@ func resetDnsIgnoreUnusableInterface(iface *net.Interface) error {
 }
 
 func resetDNS(iface *net.Interface) (err error) {
+	mainLog.Load().Debug().Str("interface", iface.Name).Msg("Resetting DNS configuration")
+
 	defer func() {
 		if err == nil {
 			return
diff --git a/config.go b/config.go
index f5e5b86..9880944 100644
--- a/config.go
+++ b/config.go
@@ -114,6 +114,9 @@ func SetConfigNameWithPath(v *viper.Viper, name, configPath string) {
 
 // InitConfig initializes default config values for given *viper.Viper instance.
 func InitConfig(v *viper.Viper, name string) {
+	logger := LoggerFromCtx(context.Background())
+	Log(context.Background(), logger.Debug(), "Config initialization started")
+
 	v.SetDefault("listener", map[string]*ListenerConfig{
 		"0": {
 			IP:   "",
@@ -152,6 +155,8 @@ func InitConfig(v *viper.Viper, name string) {
 			Timeout:     3000,
 		},
 	})
+
+	Log(context.Background(), logger.Debug(), "Config initialization completed")
 }
 
 // Config represents ctrld supported configuration.
@@ -499,7 +504,7 @@ func (uc *UpstreamConfig) ReBootstrap(ctx context.Context) {
 	_, _, _ = uc.g.Do("ReBootstrap", func() (any, error) {
 		if uc.rebootstrap.CompareAndSwap(false, true) {
 			logger := LoggerFromCtx(ctx)
-			logger.Debug().Msgf("re-bootstrapping upstream ip for %v", uc)
+			Log(ctx, logger.Debug(), "Re-bootstrapping upstream: %s", uc.Name)
 		}
 		return true, nil
 	})
@@ -823,7 +828,7 @@ func (uc *UpstreamConfig) FallbackToDirectIP(ctx context.Context) bool {
 			return
 		}
 		logger := LoggerFromCtx(ctx)
-		logger.Warn().Msgf("using direct IP for %q: %s", uc.Endpoint, ip)
+		Log(ctx, logger.Warn(), "Using direct IP for %q: %s", uc.Endpoint, ip)
 		uc.u.Host = ip
 		done = true
 	})
@@ -832,12 +837,18 @@ func (uc *UpstreamConfig) FallbackToDirectIP(ctx context.Context) bool {
 
 // Init initialized necessary values for an ListenerConfig.
 func (lc *ListenerConfig) Init() {
+	logger := LoggerFromCtx(context.Background())
+	Log(context.Background(), logger.Debug(), "Initializing listener config")
+
 	if lc.Policy != nil {
 		lc.Policy.FailoverRcodeNumbers = make([]int, len(lc.Policy.FailoverRcodes))
 		for i, rcode := range lc.Policy.FailoverRcodes {
 			lc.Policy.FailoverRcodeNumbers[i] = dnsrcode.FromString(rcode)
 		}
+		Log(context.Background(), logger.Debug(), "Listener policy initialized with %d failover rcodes", len(lc.Policy.FailoverRcodes))
 	}
+
+	Log(context.Background(), logger.Debug(), "Listener config initialization completed")
 }
 
 // ValidateConfig validates the given config.