diff --git a/cmd/portal/config.go b/cmd/portal/config.go
new file mode 100644
index 0000000..1eefeb6
--- /dev/null
+++ b/cmd/portal/config.go
@@ -0,0 +1,145 @@
+package main
+
+import (
+	"fmt"
+	"os"
+	"os/exec"
+	"path/filepath"
+	"strings"
+
+	"github.com/SpatiumPortae/portal/internal/config"
+	"github.com/alecthomas/chroma/quick"
+	homedir "github.com/mitchellh/go-homedir"
+	"github.com/spf13/cobra"
+	"github.com/spf13/viper"
+)
+
+func init() {
+	configCmd.AddCommand(configPathCmd)
+	configCmd.AddCommand(configViewCmd)
+	configCmd.AddCommand(configEditCmd)
+	configCmd.AddCommand(configResetCmd)
+}
+
+var configCmd = &cobra.Command{
+	Use:       "config",
+	Short:     "View and configure options",
+	Args:      cobra.MatchAll(cobra.ExactArgs(1), cobra.OnlyValidArgs),
+	ValidArgs: []string{configPathCmd.Name(), configViewCmd.Name(), configEditCmd.Name(), configResetCmd.Name()},
+	Run:       func(cmd *cobra.Command, args []string) {},
+}
+
+var configPathCmd = &cobra.Command{
+	Use:   "path",
+	Short: "Output the path of the config file",
+	Run: func(cmd *cobra.Command, args []string) {
+		fmt.Println(viper.ConfigFileUsed())
+	},
+}
+
+var configViewCmd = &cobra.Command{
+	Use:   "view",
+	Short: "View the configured options",
+	RunE: func(cmd *cobra.Command, args []string) error {
+		configPath := viper.ConfigFileUsed()
+		config, err := os.ReadFile(configPath)
+		if err != nil {
+			return fmt.Errorf("config file (%s) could not be read: %w", configPath, err)
+		}
+		if err := quick.Highlight(os.Stdout, string(config), "yaml", "terminal256", "onedark"); err != nil {
+			// Failed to highlight output, output un-highlighted config file contents.
+			fmt.Println(string(config))
+		}
+		return nil
+	},
+}
+
+var configEditCmd = &cobra.Command{
+	Use:   "edit",
+	Short: "Edit the configuration file",
+	RunE: func(cmd *cobra.Command, args []string) error {
+		configPath := viper.ConfigFileUsed()
+		// Strip arguments from editor variable -- allows exec.Command to lookup the editor executable correctly.
+		editor, _, _ := strings.Cut(os.Getenv("EDITOR"), " ")
+		if len(editor) == 0 {
+			//lint:ignore ST1005 error string is command output
+			return fmt.Errorf(
+				"Could not find default editor (is the $EDITOR variable set?)\nOptionally you can open the file (%s) manually", configPath,
+			)
+		}
+
+		editorCmd := exec.Command(editor, configPath)
+		editorCmd.Stdin = os.Stdin
+		editorCmd.Stdout = os.Stdout
+		editorCmd.Stderr = os.Stderr
+		if err := editorCmd.Run(); err != nil {
+			return fmt.Errorf("failed to open file (%s) in editor (%s): %w", configPath, editor, err)
+		}
+		return nil
+	},
+}
+
+var configResetCmd = &cobra.Command{
+	Use:   "reset",
+	Short: "Reset to the default configuration",
+	RunE: func(cmd *cobra.Command, args []string) error {
+		configPath := viper.ConfigFileUsed()
+		err := os.WriteFile(configPath, config.ToYaml(config.GetDefault()), 0)
+		if err != nil {
+			return fmt.Errorf("config file (%s) could not be read/written to: %w", configPath, err)
+		}
+		return nil
+	},
+}
+
+// -------------------------------------------------- Helper Functions -------------------------------------------------
+
+// initConfig initializes the viper config.
+// `config.yml` is created in $HOME/.config/portal if not already existing.
+// NOTE: The precedence levels of viper are the following: flags -> config file -> defaults.
+func initConfig() {
+	home, err := homedir.Dir()
+	if err != nil {
+		fmt.Println(err)
+		os.Exit(1)
+	}
+
+	configPath := filepath.Join(home, config.CONFIGS_DIR_NAME, config.PORTAL_CONFIG_DIR_NAME)
+	viper.AddConfigPath(configPath)
+	viper.SetConfigName(config.CONFIG_FILE_NAME)
+	viper.SetConfigType(config.CONFIG_FILE_EXT)
+
+	if err := viper.ReadInConfig(); err != nil {
+		// Create config file if not found.
+		if _, ok := err.(viper.ConfigFileNotFoundError); ok {
+			err := os.MkdirAll(configPath, os.ModePerm)
+			if err != nil {
+				fmt.Println("Could not create config directory:", err)
+				os.Exit(1)
+			}
+
+			configFile, err := os.Create(filepath.Join(configPath, fmt.Sprintf("%s.%s", config.CONFIG_FILE_NAME, config.CONFIG_FILE_EXT)))
+			if err != nil {
+				fmt.Println("Could not create config file:", err)
+				os.Exit(1)
+			}
+			defer configFile.Close()
+
+			_, err = configFile.Write(config.ToYaml(config.GetDefault()))
+			if err != nil {
+				fmt.Println("Could not write defaults to config file:", err)
+				os.Exit(1)
+			}
+		} else {
+			fmt.Println("Could not read config file:", err)
+			os.Exit(1)
+		}
+	}
+}
+
+// Sets default viper values.
+func setDefaults() {
+	for k, v := range config.ToMap(config.GetDefault()) {
+		viper.SetDefault(k, v)
+	}
+}
diff --git a/cmd/portal/constants.go b/cmd/portal/constants.go
deleted file mode 100644
index b190b0f..0000000
--- a/cmd/portal/constants.go
+++ /dev/null
@@ -1,11 +0,0 @@
-package main
-
-const CONFIG_FILE_NAME = ".portal.yml"
-
-const DEFAULT_RENDEZVOUS_ADDRESS = "167.71.65.96"
-const DEFAULT_RENDEZVOUS_PORT = 80
-
-const DEFAULT_CONFIG_YAML = `config:
-  default_rendezvous_address: 167.71.65.96
-  default_rendezvous_port: 80
-`
diff --git a/cmd/portal/main.go b/cmd/portal/main.go
index 7aa0043..fc5c411 100644
--- a/cmd/portal/main.go
+++ b/cmd/portal/main.go
@@ -1,17 +1,12 @@
 package main
 
 import (
-	"errors"
 	"fmt"
 	"io"
 	"log"
-	"net"
 	"os"
-	"path/filepath"
-	"unicode/utf8"
 
 	tea "github.com/charmbracelet/bubbletea"
-	homedir "github.com/mitchellh/go-homedir"
 	"github.com/spf13/cobra"
 	"github.com/spf13/viper"
 )
@@ -20,6 +15,22 @@ import (
 // injected at link time using -ldflags.
 var version string
 
+// Initialization of cobra and viper.
+func init() {
+	initConfig()
+	setDefaults()
+
+	rootCmd.PersistentFlags().BoolP("verbose", "v", false, "Log debug information to a file on the format `.portal-[command].log` in the current directory")
+	// Add cobra subcommands.
+	rootCmd.AddCommand(sendCmd)
+	rootCmd.AddCommand(receiveCmd)
+	rootCmd.AddCommand(serveCmd)
+	rootCmd.AddCommand(versionCmd)
+	rootCmd.AddCommand(configCmd)
+}
+
+// ------------------------------------------------------ Command ------------------------------------------------------
+
 // rootCmd is the top level `portal` command on which the other subcommands are attached to.
 var rootCmd = &cobra.Command{
 	Use:   "portal",
@@ -31,7 +42,8 @@ var rootCmd = &cobra.Command{
 }
 
 var versionCmd = &cobra.Command{
-	Use: "version",
+	Use:   "version",
+	Short: "Display the installed version of portal",
 	Run: func(cmd *cobra.Command, args []string) {
 		fmt.Println(version)
 		os.Exit(0)
@@ -45,140 +57,16 @@ func main() {
 	}
 }
 
-// Initialization of cobra and viper.
-func init() {
-	cobra.OnInitialize(initViperConfig)
-
-	rootCmd.PersistentFlags().BoolP("verbose", "v", false, "Specifes if portal logs debug information to a file on the format `.portal-[command].log` in the current directory")
-	// Setup viper config.
-	// Add cobra subcommands.
-	rootCmd.AddCommand(sendCmd)
-	rootCmd.AddCommand(receiveCmd)
-	rootCmd.AddCommand(serveCmd)
-	rootCmd.AddCommand(versionCmd)
-}
-
-// HELPER FUNCTIONS
-
-// initViperConfig initializes the viper config.
-// It creates a `.portal.yml` file at the home directory if it has not been created earlier
-// NOTE: The precedence levels of viper are the following: flags -> config file -> defaults
-// See https://github.com/spf13/viper#why-viper
-func initViperConfig() {
-	// Set default values
-	viper.SetDefault("verbose", false)
-	viper.SetDefault("rendezvousPort", DEFAULT_RENDEZVOUS_PORT)
-	viper.SetDefault("rendezvousAddress", DEFAULT_RENDEZVOUS_ADDRESS)
-
-	// Find home directory.
-	home, err := homedir.Dir()
-	if err != nil {
-		fmt.Println(err)
-		os.Exit(1)
-	}
-
-	// Search for config in home directory.
-	viper.AddConfigPath(home)
-	viper.SetConfigName(CONFIG_FILE_NAME)
-	viper.SetConfigType("yaml")
-
-	if err := viper.ReadInConfig(); err != nil {
-		// Create config file if not found
-		// NOTE: perhaps should be an empty file initially, as we would not want default IP to be written to a file on the user host
-		if _, ok := err.(viper.ConfigFileNotFoundError); ok {
-			configPath := filepath.Join(home, CONFIG_FILE_NAME)
-			configFile, err := os.Create(configPath)
-			if err != nil {
-				fmt.Println("Could not create config file:", err)
-				os.Exit(1)
-			}
-			defer configFile.Close()
-			_, err = configFile.Write([]byte(DEFAULT_CONFIG_YAML))
-			if err != nil {
-				fmt.Println("Could not write defaults to config file:", err)
-				os.Exit(1)
-			}
-		} else {
-			fmt.Println("Could not read config file:", err)
-			os.Exit(1)
-		}
-	}
-}
-
-// validateRendezvousAddressInViper validates that the `rendezvousAddress` value in viper is a valid hostname or IP
-func validateRendezvousAddressInViper() error {
-	rendezvouzAdress := net.ParseIP(viper.GetString("rendezvousAddress"))
-	err := validateHostname(viper.GetString("rendezvousAddress"))
-	// neither a valid IP nor a valid hostname was provided
-	if (rendezvouzAdress == nil) && err != nil {
-		return errors.New("invalid IP or hostname provided")
-	}
-	return nil
-}
+// -------------------------------------------------- Helper Functions -------------------------------------------------
 
 func setupLoggingFromViper(cmd string) (*os.File, error) {
 	if viper.GetBool("verbose") {
 		f, err := tea.LogToFile(fmt.Sprintf(".portal-%s.log", cmd), fmt.Sprintf("portal-%s: \n", cmd))
 		if err != nil {
-			return nil, fmt.Errorf("could not log to the provided file")
+			return nil, fmt.Errorf("could not log to the provided file: %w", err)
 		}
 		return f, nil
 	}
 	log.SetOutput(io.Discard)
 	return nil, nil
 }
-
-// validateHostname returns an error if the domain name is not valid
-// See https://tools.ietf.org/html/rfc1034#section-3.5 and
-// https://tools.ietf.org/html/rfc1123#section-2.
-// source: https://gist.github.com/chmike/d4126a3247a6d9a70922fc0e8b4f4013
-func validateHostname(name string) error {
-	switch {
-	case len(name) == 0:
-		return nil
-	case len(name) > 255:
-		return fmt.Errorf("name length is %d, can't exceed 255", len(name))
-	}
-	var l int
-	for i := 0; i < len(name); i++ {
-		b := name[i]
-		if b == '.' {
-			// check domain labels validity
-			switch {
-			case i == l:
-				return fmt.Errorf("invalid character '%c' at offset %d: label can't begin with a period", b, i)
-			case i-l > 63:
-				return fmt.Errorf("byte length of label '%s' is %d, can't exceed 63", name[l:i], i-l)
-			case name[l] == '-':
-				return fmt.Errorf("label '%s' at offset %d begins with a hyphen", name[l:i], l)
-			case name[i-1] == '-':
-				return fmt.Errorf("label '%s' at offset %d ends with a hyphen", name[l:i], l)
-			}
-			l = i + 1
-			continue
-		}
-		// test label character validity, note: tests are ordered by decreasing validity frequency
-		if !(b >= 'a' && b <= 'z' || b >= '0' && b <= '9' || b == '-' || b >= 'A' && b <= 'Z') {
-			// show the printable unicode character starting at byte offset i
-			c, _ := utf8.DecodeRuneInString(name[i:])
-			if c == utf8.RuneError {
-				return fmt.Errorf("invalid rune at offset %d", i)
-			}
-			return fmt.Errorf("invalid character '%c' at offset %d", c, i)
-		}
-	}
-	// check top level domain validity
-	switch {
-	case l == len(name):
-		return fmt.Errorf("missing top level domain, domain can't end with a period")
-	case len(name)-l > 63:
-		return fmt.Errorf("byte length of top level domain '%s' is %d, can't exceed 63", name[l:], len(name)-l)
-	case name[l] == '-':
-		return fmt.Errorf("top level domain '%s' at offset %d begins with a hyphen", name[l:], l)
-	case name[len(name)-1] == '-':
-		return fmt.Errorf("top level domain '%s' at offset %d ends with a hyphen", name[l:], l)
-	case name[l] >= '0' && name[l] <= '9':
-		return fmt.Errorf("top level domain '%s' at offset %d begins with a digit", name[l:], l)
-	}
-	return nil
-}
diff --git a/cmd/portal/receive.go b/cmd/portal/receive.go
index b39d203..b511841 100644
--- a/cmd/portal/receive.go
+++ b/cmd/portal/receive.go
@@ -16,6 +16,20 @@ import (
 	"golang.org/x/exp/slices"
 )
 
+// Setup flags.
+func init() {
+	// Add subcommand flags (dummy default values as default values are handled through viper)
+	desc := `Address of relay server. Accepted formats:
+  - 127.0.0.1:8080
+  - [::1]:8080
+  - somedomain.com
+	`
+	receiveCmd.Flags().StringP("relay", "r", "", desc)
+	receiveCmd.Flags().BoolP("yes", "y", false, "Overwrite existing files without [Y/n] prompts")
+}
+
+// ------------------------------------------------------ Command ------------------------------------------------------
+
 // receiveCmd is the cobra command for `portal receive`
 var receiveCmd = &cobra.Command{
 	Use:               "receive",
@@ -23,18 +37,29 @@ var receiveCmd = &cobra.Command{
 	Long:              "The receive command receives files from the sender with the matching password.",
 	Args:              cobra.ExactArgs(1),
 	ValidArgsFunction: passwordCompletion,
-	PreRun: func(cmd *cobra.Command, args []string) {
-		// Bind flags to viper
-		//nolint
-		viper.BindPFlag("rendezvousPort", cmd.Flags().Lookup("rendezvous-port"))
-		//nolint
-		viper.BindPFlag("rendezvousAddress", cmd.Flags().Lookup("rendezvous-address"))
+	PreRunE: func(cmd *cobra.Command, args []string) error {
+		// Bind flags to viper.
+		if err := viper.BindPFlag("relay", cmd.Flags().Lookup("relay")); err != nil {
+			return fmt.Errorf("binding relay flag: %w", err)
+		}
+
+		// Reverse the --yes/-y flag value as it has an inverse relationship
+		// with the configuration value 'prompt_overwrite_files'.
+		overwriteFlag := cmd.Flags().Lookup("yes")
+		if overwriteFlag.Changed {
+			shouldOverwrite, _ := strconv.ParseBool(overwriteFlag.Value.String())
+			_ = overwriteFlag.Value.Set(strconv.FormatBool(!shouldOverwrite))
+		}
+
+		if err := viper.BindPFlag("prompt_overwrite_files", overwriteFlag); err != nil {
+			return fmt.Errorf("binding yes flag: %w", err)
+		}
+		return nil
 	},
 	RunE: func(cmd *cobra.Command, args []string) error {
 		file.RemoveTemporaryFiles(file.RECEIVE_TEMP_FILE_NAME_PREFIX)
-		err := validateRendezvousAddressInViper()
-		if err != nil {
-			return err
+		if err := validateRelayInViper(); err != nil {
+			return fmt.Errorf("%w (%s) is not a valid address", err, viper.GetString("relay"))
 		}
 		logFile, err := setupLoggingFromViper("receive")
 		if err != nil {
@@ -50,24 +75,16 @@ var receiveCmd = &cobra.Command{
 	},
 }
 
-// Setup flags.
-func init() {
-	// Add subcommand flags (dummy default values as default values are handled through viper).
-	// TODO: recactor this into a single flag for providing a TCPAddr.
-	receiveCmd.Flags().IntP("rendezvous-port", "p", 0, "port on which the rendezvous server is running")
-	receiveCmd.Flags().StringP("rendezvous-address", "a", "", "host address for the rendezvous server")
-}
+// ------------------------------------------------------ Handler ------------------------------------------------------
 
 // handleReceiveCommand is the receive application.
 func handleReceiveCommand(password string) {
-	addr := viper.GetString("rendezvousAddress")
-	port := viper.GetInt("rendezvousPort")
 	var opts []receiver.Option
 	ver, err := semver.Parse(version)
 	if err == nil {
 		opts = append(opts, receiver.WithVersion(ver))
 	}
-	receiver := receiver.New(fmt.Sprintf("%s:%d", addr, port), password, opts...)
+	receiver := receiver.New(viper.GetString("relay"), password, opts...)
 
 	if _, err := receiver.Run(); err != nil {
 		fmt.Println("Error initializing UI", err)
diff --git a/cmd/portal/send.go b/cmd/portal/send.go
index 277f561..92c9e13 100644
--- a/cmd/portal/send.go
+++ b/cmd/portal/send.go
@@ -12,26 +12,41 @@ import (
 	"github.com/spf13/viper"
 )
 
+// Set flags.
+func init() {
+	// Add subcommand flags (dummy default values as default values are handled through viper)
+	desc := `Address of relay server. Accepted formats:
+  - 127.0.0.1:8080
+  - [::1]:8080
+  - somedomain.com
+	`
+	sendCmd.Flags().StringP("relay", "r", "", desc)
+}
+
+// ------------------------------------------------------ Command ------------------------------------------------------
+
 // sendCmd cobra command for `portal send`.
 var sendCmd = &cobra.Command{
 	Use:   "send",
 	Short: "Send one or more files",
 	Long:  "The send command adds one or more files to be sent. Files are archived and compressed before sending.",
 	Args:  cobra.MinimumNArgs(1),
-	PreRun: func(cmd *cobra.Command, args []string) {
+	PreRunE: func(cmd *cobra.Command, args []string) error {
 		// Bind flags to viper
-		//nolint:errcheck
-		viper.BindPFlag("rendezvousPort", cmd.Flags().Lookup("rendezvous-port"))
-		//nolint:errcheck
-		viper.BindPFlag("rendezvousAddress", cmd.Flags().Lookup("rendezvous-address"))
+		if err := viper.BindPFlag("relay", cmd.Flags().Lookup("relay")); err != nil {
+			return fmt.Errorf("binding relay flag: %w", err)
+		}
+		return nil
+
 	},
 	RunE: func(cmd *cobra.Command, args []string) error {
 		if err := sender.Init(); err != nil {
 			return err
 		}
 		file.RemoveTemporaryFiles(file.SEND_TEMP_FILE_NAME_PREFIX)
-		if err := validateRendezvousAddressInViper(); err != nil {
-			return err
+
+		if err := validateRelayInViper(); err != nil {
+			return fmt.Errorf("%w (%s) is not a valid address", err, viper.GetString("relay"))
 		}
 
 		logFile, err := setupLoggingFromViper("send")
@@ -45,25 +60,18 @@ var sendCmd = &cobra.Command{
 	},
 }
 
-// Set flags.
-func init() {
-	// Add subcommand flags (dummy default values as default values are handled through viper)
-	//TODO: refactor into a single flag providing a string
-	sendCmd.Flags().IntP("rendezvous-port", "p", 0, "port on which the rendezvous server is running")
-	sendCmd.Flags().StringP("rendezvous-address", "a", "", "host address for the rendezvous server")
-}
+// ------------------------------------------------------ Handler ------------------------------------------------------
 
 // handleSendCommand is the sender application.
 func handleSendCommand(fileNames []string) {
-	addr := viper.GetString("rendezvousAddress")
-	port := viper.GetInt("rendezvousPort")
 	var opts []senderui.Option
 	ver, err := semver.Parse(version)
 	// Conditionally add option to sender ui
 	if err == nil {
 		opts = append(opts, senderui.WithVersion(ver))
 	}
-	sender := senderui.New(fileNames, fmt.Sprintf("%s:%d", addr, port), opts...)
+	relayAddr := viper.GetString("relay")
+	sender := senderui.New(fileNames, relayAddr, opts...)
 	if _, err := sender.Run(); err != nil {
 		fmt.Println("Error initializing UI", err)
 		os.Exit(1)
diff --git a/cmd/portal/serve.go b/cmd/portal/serve.go
index bd5a132..196c63d 100644
--- a/cmd/portal/serve.go
+++ b/cmd/portal/serve.go
@@ -8,12 +8,18 @@ import (
 	"github.com/spf13/cobra"
 )
 
+// NOTE: The `port` flag is required and not managed through viper.
+func init() {
+	serveCmd.Flags().IntP("port", "p", 0, "port to run the portal relay server on")
+	_ = serveCmd.MarkFlagRequired("port")
+}
+
 // serveCmd is the cobra command for `portal serve`
 var serveCmd = &cobra.Command{
 	Use:   "serve",
-	Short: "Serve the rendezvous-server",
-	Long:  "The serve command serves the rendezvous-server locally.",
-	Args:  cobra.NoArgs,
+	Short: "Serve the relay server",
+	Long:  "The serve command serves the relay server locally.",
+	Args:  cobra.MatchAll(cobra.ExactArgs(0), cobra.NoArgs),
 	RunE: func(cmd *cobra.Command, args []string) error {
 		port, _ := cmd.Flags().GetInt("port")
 		ver, err := semver.Parse(version)
@@ -25,10 +31,3 @@ var serveCmd = &cobra.Command{
 		return nil
 	},
 }
-
-// Add `port` flag.
-// NOTE: The `port` flag is required and not managed through viper.
-func init() {
-	serveCmd.Flags().IntP("port", "p", 0, "port to run the portal rendezvous server on")
-	_ = serveCmd.MarkFlagRequired("port")
-}
diff --git a/cmd/portal/validate.go b/cmd/portal/validate.go
new file mode 100644
index 0000000..f3543e4
--- /dev/null
+++ b/cmd/portal/validate.go
@@ -0,0 +1,71 @@
+package main
+
+import (
+	"errors"
+	"net"
+	"regexp"
+	"strconv"
+	"strings"
+
+	"github.com/spf13/viper"
+	"golang.org/x/net/idna"
+)
+
+var ErrInvalidRelay = errors.New("invalid relay address provided")
+
+var ipv6Rex = regexp.MustCompile(`\[(.*?)\]`)
+
+func stripPort(addr string) string {
+	split := strings.Split(addr, ":")
+	if len(split) == 2 {
+		return split[0]
+	}
+
+	matches := ipv6Rex.FindStringSubmatch(addr)
+	if len(matches) >= 2 {
+		return matches[1]
+	}
+	return addr
+}
+
+// validateRelayInViper validates that the `relay` value in viper is a valid hostname or IP
+func validateRelayInViper() error {
+	relayAddr := viper.GetString("relay")
+
+	onlyHost := stripPort(relayAddr)
+
+	// Port is present, validate it.
+	if relayAddr != onlyHost {
+		_, port, err := net.SplitHostPort(relayAddr)
+		if err != nil {
+			return ErrInvalidRelay
+		}
+		portNumber, err := strconv.Atoi(port)
+		if err != nil {
+			return ErrInvalidRelay
+		}
+		if portNumber < 1 || portNumber > 65535 {
+			return ErrInvalidRelay
+		}
+	}
+
+	// Only port is present, and was valid -- accept an address like ":5432".
+	if len(relayAddr) > 0 && len(onlyHost) == 0 {
+		return nil
+	}
+
+	// On the form localhost or localhost:1234, valid.
+	if onlyHost == "localhost" {
+		return nil
+	}
+
+	if ip := net.ParseIP(onlyHost); ip != nil {
+		return nil
+	}
+
+	if _, err := idna.Lookup.ToASCII(relayAddr); err == nil {
+		return nil
+	}
+
+	return ErrInvalidRelay
+}
diff --git a/go.mod b/go.mod
index 894b48b..7cea214 100644
--- a/go.mod
+++ b/go.mod
@@ -3,11 +3,14 @@ module github.com/SpatiumPortae/portal
 go 1.18
 
 require (
+	github.com/alecthomas/chroma v0.10.0
 	github.com/atotto/clipboard v0.1.4
 	github.com/charmbracelet/bubbles v0.15.0
 	github.com/charmbracelet/bubbletea v0.23.2
 	github.com/charmbracelet/lipgloss v0.6.0
 	github.com/docker/go-connections v0.4.0
+	github.com/erikgeiser/promptkit v0.8.0
+	github.com/fatih/structs v1.1.0
 	github.com/klauspost/pgzip v1.2.5
 	github.com/mattn/go-runewidth v0.0.14
 	github.com/mitchellh/go-homedir v1.1.0
@@ -17,6 +20,7 @@ require (
 	github.com/stretchr/testify v1.8.1
 	github.com/testcontainers/testcontainers-go v0.13.0
 	go.uber.org/zap v1.24.0
+	golang.org/x/net v0.7.0
 	nhooyr.io/websocket v1.8.7
 )
 
@@ -45,6 +49,7 @@ require (
 	github.com/containerd/cgroups v1.0.3 // indirect
 	github.com/containerd/containerd v1.5.18 // indirect
 	github.com/davecgh/go-spew v1.1.1 // indirect
+	github.com/dlclark/regexp2 v1.4.0 // indirect
 	github.com/docker/distribution v2.8.0+incompatible // indirect
 	github.com/docker/docker v20.10.11+incompatible // indirect
 	github.com/docker/go-units v0.4.0 // indirect
@@ -70,7 +75,6 @@ require (
 	go.opencensus.io v0.24.0 // indirect
 	go.uber.org/atomic v1.10.0 // indirect
 	go.uber.org/multierr v1.9.0 // indirect
-	golang.org/x/net v0.7.0 // indirect
 	golang.org/x/sync v0.1.0 // indirect
 	google.golang.org/genproto v0.0.0-20221227171554-f9683d7f8bef // indirect
 	google.golang.org/grpc v1.52.0 // indirect
diff --git a/go.sum b/go.sum
index d6825b6..909b151 100644
--- a/go.sum
+++ b/go.sum
@@ -80,6 +80,8 @@ github.com/OneOfOne/xxhash v1.2.2/go.mod h1:HSdplMjZKSmBqAxg5vPj2TmRDmfkzw+cTzAE
 github.com/PuerkitoBio/purell v1.1.1/go.mod h1:c11w/QuzBsJSee3cPx9rAFu61PvFxuPbtSwDGJws/X0=
 github.com/PuerkitoBio/urlesc v0.0.0-20170810143723-de5bf2ad4578/go.mod h1:uGdkoq3SwY9Y+13GIhn11/XLaGBb4BfwItxLd5jeuXE=
 github.com/Shopify/logrus-bugsnag v0.0.0-20171204204709-577dee27f20d/go.mod h1:HI8ITrYtUY+O+ZhtlqUnD8+KwNPOyugEhfP9fdUIaEQ=
+github.com/alecthomas/chroma v0.10.0 h1:7XDcGkCQopCNKjZHfYrNLraA+M7e0fMiJ/Mfikbfjek=
+github.com/alecthomas/chroma v0.10.0/go.mod h1:jtJATyUxlIORhUOFNA9NZDWGAQ8wpxQQqNSB4rjA/1s=
 github.com/alecthomas/template v0.0.0-20160405071501-a0175ee3bccc/go.mod h1:LOuyumcjzFXgccqObfd/Ljyb9UuFJ6TxHnclSeseNhc=
 github.com/alecthomas/template v0.0.0-20190718012654-fb15b899a751/go.mod h1:LOuyumcjzFXgccqObfd/Ljyb9UuFJ6TxHnclSeseNhc=
 github.com/alecthomas/units v0.0.0-20151022065526-2efee857e7cf/go.mod h1:ybxpYRFXyAe+OPACYpWeL0wqObRcbAqCMya13uyzqw0=
@@ -265,6 +267,8 @@ github.com/denverdino/aliyungo v0.0.0-20190125010748-a747050bb1ba/go.mod h1:dV8l
 github.com/dgrijalva/jwt-go v0.0.0-20170104182250-a601269ab70c/go.mod h1:E3ru+11k8xSBh+hMPgOLZmtrrCbhqsmaPHjLKYnJCaQ=
 github.com/dgrijalva/jwt-go v3.2.0+incompatible/go.mod h1:E3ru+11k8xSBh+hMPgOLZmtrrCbhqsmaPHjLKYnJCaQ=
 github.com/dgryski/go-sip13 v0.0.0-20181026042036-e10d5fee7954/go.mod h1:vAd38F8PWV+bWy6jNmig1y/TA+kYO4g3RSRF0IAv0no=
+github.com/dlclark/regexp2 v1.4.0 h1:F1rxgk7p4uKjwIQxBs9oAXe5CqrXlCduYEJvrF4u93E=
+github.com/dlclark/regexp2 v1.4.0/go.mod h1:2pZnwuY/m+8K6iRw6wQdMtk+rH5tNGR1i55kozfMjCc=
 github.com/dnaeon/go-vcr v1.0.1/go.mod h1:aBB1+wY4s93YsC3HHjMBMrwTj2R9FHDzUr9KyGc8n1E=
 github.com/dnephin/pflag v1.0.7/go.mod h1:uxE91IoWURlOiTUIA8Mq5ZZkAv3dPUfZNaT80Zm7OQE=
 github.com/docker/distribution v0.0.0-20190905152932-14b96e55d84c/go.mod h1:0+TTO4EOBfRPhZXAeF1Vu+W3hHZ8eLp8PgKVZlcvtFY=
@@ -296,9 +300,13 @@ github.com/envoyproxy/go-control-plane v0.9.4/go.mod h1:6rpuAdCZL397s3pYoYcLgu1m
 github.com/envoyproxy/go-control-plane v0.9.7/go.mod h1:cwu0lG7PUMfa9snN8LXBig5ynNVH9qI8YYLbd1fK2po=
 github.com/envoyproxy/go-control-plane v0.9.9-0.20201210154907-fd9021fe5dad/go.mod h1:cXg6YxExXjJnVBQHBLXeUAgxn2UodCpnH306RInaBQk=
 github.com/envoyproxy/protoc-gen-validate v0.1.0/go.mod h1:iSmxcyjqTsJpI2R4NaDN7+kN2VEUnK/pcBlmesArF7c=
+github.com/erikgeiser/promptkit v0.8.0 h1:bvOzPs6RLyfRZDSgVWOghQEiBSRHQ3zmDdxcV8zOc+E=
+github.com/erikgeiser/promptkit v0.8.0/go.mod h1:QxyFbCrrj20PyvV5b+ckWPozbgX11s04GeRlmTCIMTo=
 github.com/evanphx/json-patch v4.9.0+incompatible/go.mod h1:50XU6AFN0ol/bzJsmQLiYLvXMP4fmwYFNcr97nuDLSk=
 github.com/fatih/color v1.7.0/go.mod h1:Zm6kSWBoL9eyXnKyktHP6abPY2pDugNf5KwzbycvMj4=
 github.com/fatih/color v1.10.0/go.mod h1:ELkj/draVOlAH/xkhN6mQ50Qd0MPOk5AAr3maGEBuJM=
+github.com/fatih/structs v1.1.0 h1:Q7juDM0QtcnhCpeyLGQKyg4TOIghuNXrkL32pHAUMxo=
+github.com/fatih/structs v1.1.0/go.mod h1:9NiDSp5zOcgEDl+j00MP/WkGVPOlPRLejGD8Ga6PJ7M=
 github.com/form3tech-oss/jwt-go v3.2.2+incompatible/go.mod h1:pbq4aXjuKjdthFRnoDwaVPLA+WlJuPGy+QneDUgJi2k=
 github.com/frankban/quicktest v1.11.3/go.mod h1:wRf/ReqHper53s+kmmSZizM8NamnL3IM0I9ntUbOk+k=
 github.com/frankban/quicktest v1.14.3 h1:FJKSZTDHjyhriyC81FLQ0LY93eSai0ZyR/ZIkd3ZUKE=
diff --git a/internal/config/config.go b/internal/config/config.go
new file mode 100644
index 0000000..3be111d
--- /dev/null
+++ b/internal/config/config.go
@@ -0,0 +1,52 @@
+package config
+
+import (
+	"fmt"
+	"strings"
+
+	"github.com/fatih/structs"
+	"github.com/spf13/viper"
+)
+
+const CONFIGS_DIR_NAME = ".config"
+const PORTAL_CONFIG_DIR_NAME = "portal"
+const CONFIG_FILE_NAME = "config"
+const CONFIG_FILE_EXT = "yml"
+
+type Config struct {
+	Relay                string `mapstructure:"relay"`
+	Verbose              bool   `mapstructure:"verbose"`
+	PromptOverwriteFiles bool   `mapstructure:"prompt_overwrite_files"`
+}
+
+func GetDefault() Config {
+	return Config{
+		Relay:                "167.71.65.96:80",
+		Verbose:              false,
+		PromptOverwriteFiles: true,
+	}
+}
+
+func ToMap(config Config) map[string]any {
+	m := map[string]any{}
+	for _, field := range structs.Fields(config) {
+		key := field.Tag("mapstructure")
+		value := field.Value()
+		m[key] = value
+	}
+	return m
+}
+
+func ToYaml(config Config) []byte {
+	var builder strings.Builder
+	for k, v := range ToMap(config) {
+		builder.WriteString(fmt.Sprintf("%s: %v", k, v))
+		builder.WriteRune('\n')
+	}
+	return []byte(builder.String())
+}
+
+func IsDefault(key string) bool {
+	defaults := ToMap(GetDefault())
+	return viper.Get(key) == defaults[key]
+}
diff --git a/internal/file/file.go b/internal/file/file.go
index 9ced7c7..d800e12 100644
--- a/internal/file/file.go
+++ b/internal/file/file.go
@@ -15,6 +15,8 @@ import (
 const SEND_TEMP_FILE_NAME_PREFIX = "portal-send-temp"
 const RECEIVE_TEMP_FILE_NAME_PREFIX = "portal-receive-temp"
 
+type OverwriteDecider func(fileName string) (bool, error)
+
 func ReadFiles(fileNames []string) ([]*os.File, error) {
 	var files []*os.File
 	for _, fileName := range fileNames {
@@ -27,9 +29,9 @@ func ReadFiles(fileNames []string) ([]*os.File, error) {
 	return files, nil
 }
 
-// ArchiveAndCompressFiles tars and gzip-compresses files into a temporary file, returning it
+// PackFiles tars and gzip-compresses files into a temporary file, returning it
 // along with the resulting size
-func ArchiveAndCompressFiles(files []*os.File) (*os.File, int64, error) {
+func PackFiles(files []*os.File) (*os.File, int64, error) {
 	// chained writers -> writing to tw writes to gw -> writes to temporary file
 	tempFile, err := os.CreateTemp(os.TempDir(), SEND_TEMP_FILE_NAME_PREFIX)
 	if err != nil {
@@ -60,9 +62,9 @@ func ArchiveAndCompressFiles(files []*os.File) (*os.File, int64, error) {
 	return tempFile, fileInfo.Size(), nil
 }
 
-// DecompressAndUnarchiveBytes gzip-decompresses and un-tars files into the current working directory
+// UnpackFiles gzip-decompresses and un-tars files into the current working directory
 // and returns the names and decompressed size of the created files
-func DecompressAndUnarchiveBytes(reader io.Reader) ([]string, int64, error) {
+func UnpackFiles(reader io.Reader, decideOverwrite OverwriteDecider) ([]string, int64, error) {
 	// chained readers -> gr reads from reader -> tr reads from gr
 	gr, err := pgzip.NewReader(reader)
 	if err != nil {
@@ -94,24 +96,39 @@ func DecompressAndUnarchiveBytes(reader io.Reader) ([]string, int64, error) {
 		fileTarget := filepath.Join(cwd, header.Name)
 
 		switch header.Typeflag {
+
 		case tar.TypeDir:
 			if _, err := os.Stat(fileTarget); err != nil {
 				if err := os.MkdirAll(fileTarget, 0755); err != nil {
 					return nil, 0, err
 				}
 			}
+
 		case tar.TypeReg:
+			if fileExists(fileTarget) {
+				shouldOverwrite, err := decideOverwrite(fileTarget)
+				if err != nil {
+					return nil, 0, err
+				}
+				if !shouldOverwrite {
+					continue
+				}
+			}
+
 			f, err := os.OpenFile(fileTarget, os.O_CREATE|os.O_RDWR, os.FileMode(header.Mode))
 			if err != nil {
 				return nil, 0, err
 			}
+
 			if _, err := io.Copy(f, tr); err != nil {
 				return nil, 0, err
 			}
+
 			fileInfo, err := f.Stat()
 			if err != nil {
 				return nil, 0, err
 			}
+
 			decompressedSize += fileInfo.Size()
 			createdFiles = append(createdFiles, header.Name)
 			f.Close()
@@ -195,6 +212,11 @@ func addToTarArchive(tw *tar.Writer, file *os.File) error {
 	})
 }
 
+func fileExists(filename string) bool {
+	_, err := os.Stat(filename)
+	return !os.IsNotExist(err)
+}
+
 // optimistically remove files created by portal with the specified prefix
 func RemoveTemporaryFiles(prefix string) {
 	tempFiles, err := os.ReadDir(os.TempDir())
diff --git a/ui/constants.go b/ui/constants.go
index 3ed634e..97afd17 100644
--- a/ui/constants.go
+++ b/ui/constants.go
@@ -26,10 +26,13 @@ const (
 )
 
 type KeyMap struct {
-	Quit         key.Binding
-	CopyPassword key.Binding
-	FileListUp   key.Binding
-	FileListDown key.Binding
+	Quit                   key.Binding
+	CopyPassword           key.Binding
+	FileListUp             key.Binding
+	FileListDown           key.Binding
+	OverwritePromptYes     key.Binding
+	OverwritePromptNo      key.Binding
+	OverwritePromptConfirm key.Binding
 }
 
 func (k KeyMap) ShortHelp() []key.Binding {
@@ -38,12 +41,23 @@ func (k KeyMap) ShortHelp() []key.Binding {
 		k.CopyPassword,
 		k.FileListUp,
 		k.FileListDown,
+		k.OverwritePromptYes,
+		k.OverwritePromptNo,
+		k.OverwritePromptConfirm,
 	}
 }
 
 func (k KeyMap) FullHelp() [][]key.Binding {
 	return [][]key.Binding{
-		{k.Quit, k.CopyPassword, k.FileListUp, k.FileListDown},
+		{
+			k.Quit,
+			k.CopyPassword,
+			k.FileListUp,
+			k.FileListDown,
+			k.OverwritePromptYes,
+			k.OverwritePromptNo,
+			k.OverwritePromptConfirm,
+		},
 	}
 }
 
@@ -73,6 +87,21 @@ var Keys = KeyMap{
 		key.WithHelp("(↓/j)", "file summary down"),
 		key.WithDisabled(),
 	),
+	OverwritePromptYes: key.NewBinding(
+		key.WithKeys("y", "Y"),
+		key.WithHelp("(Y/y)", "accept overwrite"),
+		key.WithDisabled(),
+	),
+	OverwritePromptNo: key.NewBinding(
+		key.WithKeys("n", "N"),
+		key.WithHelp("(N/n)", "deny overwrite"),
+		key.WithDisabled(),
+	),
+	OverwritePromptConfirm: key.NewBinding(
+		key.WithKeys("enter"),
+		key.WithHelp("(⏎ )", "confirm choice"),
+		key.WithDisabled(),
+	),
 }
 
 var PadText = strings.Repeat(" ", MARGIN)
diff --git a/ui/filetable/filetable.go b/ui/filetable/filetable.go
index d23f701..82f3d3a 100644
--- a/ui/filetable/filetable.go
+++ b/ui/filetable/filetable.go
@@ -162,5 +162,8 @@ func (m Model) Update(msg tea.Msg) (tea.Model, tea.Cmd) {
 }
 
 func (m Model) View() string {
+	if len(m.rows) == 0 {
+		return ""
+	}
 	return fileTableStyle.Render(m.table.View()) + "\n\n"
 }
diff --git a/ui/receiver/receiver.go b/ui/receiver/receiver.go
index 064c386..7cd5437 100644
--- a/ui/receiver/receiver.go
+++ b/ui/receiver/receiver.go
@@ -21,6 +21,9 @@ import (
 	"github.com/charmbracelet/bubbles/spinner"
 	tea "github.com/charmbracelet/bubbletea"
 	"github.com/charmbracelet/lipgloss"
+	"github.com/erikgeiser/promptkit"
+	"github.com/erikgeiser/promptkit/confirmation"
+	"github.com/spf13/viper"
 )
 
 // ------------------------------------------------------ Ui State -----------------------------------------------------
@@ -31,6 +34,7 @@ const (
 	showEstablishing uiState = iota
 	showReceivingProgress
 	showDecompressing
+	showOverwritePrompt
 	showFinished
 )
 
@@ -47,8 +51,16 @@ type receiveDoneMsg struct {
 	temp *os.File
 }
 
+type overwritePromptRequestMsg struct {
+	fileName string
+}
+
+type overwritePromptResponseMsg struct {
+	shouldOverwrite bool
+}
+
 type decompressionDoneMsg struct {
-	filenames               []string
+	fileNames               []string
 	decompressedPayloadSize int64
 }
 
@@ -67,8 +79,10 @@ type model struct {
 	transferType transfer.Type
 	password     string
 
-	ctx  context.Context
-	msgs chan interface{}
+	ctx                      context.Context
+	msgs                     chan interface{}
+	overwritePromptRequests  chan overwritePromptRequestMsg
+	overwritePromptResponses chan overwritePromptResponseMsg
 
 	rendezvousAddr string
 
@@ -81,6 +95,7 @@ type model struct {
 	spinner          spinner.Model
 	transferProgress transferprogress.Model
 	fileTable        filetable.Model
+	overwritePrompt  confirmation.Model
 	help             help.Model
 	keys             ui.KeyMap
 }
@@ -88,14 +103,17 @@ type model struct {
 // New creates a new receiver program.
 func New(addr string, password string, opts ...Option) *tea.Program {
 	m := model{
-		transferProgress: transferprogress.New(),
-		msgs:             make(chan interface{}, 10),
-		fileTable:        filetable.New(),
-		password:         password,
-		rendezvousAddr:   addr,
-		help:             help.New(),
-		keys:             ui.Keys,
-		ctx:              context.Background(),
+		transferProgress:         transferprogress.New(),
+		msgs:                     make(chan interface{}, 10),
+		overwritePromptRequests:  make(chan overwritePromptRequestMsg),
+		overwritePromptResponses: make(chan overwritePromptResponseMsg),
+		password:                 password,
+		rendezvousAddr:           addr,
+		fileTable:                filetable.New(),
+		overwritePrompt:          *confirmation.NewModel(confirmation.New("", confirmation.Undecided)),
+		help:                     help.New(),
+		keys:                     ui.Keys,
+		ctx:                      context.Background(),
 	}
 	for _, opt := range opts {
 		opt(&m)
@@ -173,6 +191,7 @@ func (m model) Update(msg tea.Msg) (tea.Model, tea.Cmd) {
 	case receiveDoneMsg:
 		m.state = showDecompressing
 		m.resetSpinner()
+
 		message := fmt.Sprintf("Transfer completed in %s with average transfer speed %s/s",
 			time.Since(m.transferProgress.TransferStartTime).Round(time.Millisecond).String(),
 			ui.ByteCountSI(m.transferProgress.TransferSpeedEstimateBps),
@@ -180,11 +199,26 @@ func (m model) Update(msg tea.Msg) (tea.Model, tea.Cmd) {
 
 		m.fileTable.SetMaxHeight(math.MaxInt)
 		m.fileTable = m.fileTable.Finalize().(filetable.Model)
-		return m, ui.TaskCmd(message, tea.Batch(m.spinner.Tick, decompressCmd(msg.temp)))
+
+		cmds := []tea.Cmd{m.spinner.Tick,
+			m.listenOverwritePromptRequestsCmd(),
+			m.decompressCmd(msg.temp),
+		}
+
+		return m, ui.TaskCmd(message, tea.Batch(cmds...))
+
+	case overwritePromptRequestMsg:
+		m.state = showOverwritePrompt
+		m.resetSpinner()
+		m.keys.OverwritePromptYes.SetEnabled(true)
+		m.keys.OverwritePromptNo.SetEnabled(true)
+		m.keys.OverwritePromptConfirm.SetEnabled(true)
+
+		return m, tea.Batch(m.spinner.Tick, m.newOverwritePrompt(msg.fileName))
 
 	case decompressionDoneMsg:
 		m.state = showFinished
-		m.receivedFiles = msg.filenames
+		m.receivedFiles = msg.fileNames
 		m.decompressedPayloadSize = msg.decompressedPayloadSize
 
 		m.fileTable.SetFiles(m.receivedFiles)
@@ -194,6 +228,7 @@ func (m model) Update(msg tea.Msg) (tea.Model, tea.Cmd) {
 		return m, ui.ErrorCmd(errors.New(msg.Error()))
 
 	case tea.KeyMsg:
+		var cmds []tea.Cmd
 		switch {
 		case key.Matches(msg, m.keys.Quit):
 			return m, tea.Quit
@@ -201,21 +236,46 @@ func (m model) Update(msg tea.Msg) (tea.Model, tea.Cmd) {
 
 		fileTableModel, fileTableCmd := m.fileTable.Update(msg)
 		m.fileTable = fileTableModel.(filetable.Model)
+		cmds = append(cmds, fileTableCmd)
+
+		_, promptCmd := m.overwritePrompt.Update(msg)
+		if m.state == showOverwritePrompt {
+			switch msg.String() {
+			case "left", "right":
+				cmds = append(cmds, promptCmd)
+			}
+			switch {
+			case key.Matches(msg, m.keys.OverwritePromptYes, m.keys.OverwritePromptNo, m.keys.OverwritePromptConfirm):
+				m.state = showDecompressing
+				m.keys.OverwritePromptYes.SetEnabled(false)
+				m.keys.OverwritePromptNo.SetEnabled(false)
+				m.keys.OverwritePromptConfirm.SetEnabled(false)
+				shouldOverwrite, _ := m.overwritePrompt.Value()
+				m.overwritePromptResponses <- overwritePromptResponseMsg{shouldOverwrite}
+				cmds = append(cmds, m.listenOverwritePromptRequestsCmd())
+			}
+		}
 
-		return m, fileTableCmd
+		return m, tea.Batch(cmds...)
 
 	case tea.WindowSizeMsg:
 		m.width = msg.Width
 		transferProgressModel, transferProgressCmd := m.transferProgress.Update(msg)
 		m.transferProgress = transferProgressModel.(transferprogress.Model)
+
 		fileTableModel, fileTableCmd := m.fileTable.Update(msg)
 		m.fileTable = fileTableModel.(filetable.Model)
-		return m, tea.Batch(transferProgressCmd, fileTableCmd)
+
+		m.overwritePrompt.MaxWidth = msg.Width - 2*ui.MARGIN - 4
+		_, promptCmd := m.overwritePrompt.Update(msg)
+
+		return m, tea.Batch(transferProgressCmd, fileTableCmd, promptCmd)
 
 	default:
-		var cmd tea.Cmd
-		m.spinner, cmd = m.spinner.Update(msg)
-		return m, cmd
+		var spinnerCmd tea.Cmd
+		m.spinner, spinnerCmd = m.spinner.Update(msg)
+		_, promptCmd := m.overwritePrompt.Update(msg)
+		return m, tea.Batch(spinnerCmd, promptCmd)
 	}
 }
 
@@ -243,6 +303,14 @@ func (m model) View() string {
 			ui.PadText + m.transferProgress.View() + "\n\n" +
 			ui.PadText + m.help.View(m.keys) + "\n\n"
 
+	case showOverwritePrompt:
+		waitingText := fmt.Sprintf("%s Waiting for file overwrite confirmation", m.spinner.View())
+		return ui.PadText + ui.LogSeparator(m.width) +
+			ui.PadText + ui.InfoStyle(waitingText) + "\n\n" +
+			ui.PadText + m.transferProgress.View() + "\n\n" +
+			ui.PadText + m.overwritePrompt.View() + "\n\n" +
+			ui.PadText + m.help.View(m.keys) + "\n\n"
+
 	case showDecompressing:
 		payloadSize := ui.BoldText(ui.ByteCountSI(m.payloadSize))
 		decompressingText := fmt.Sprintf("%s Decompressing payload (%s compressed) and writing to disk", m.spinner.View(), payloadSize)
@@ -253,10 +321,10 @@ func (m model) View() string {
 
 	case showFinished:
 		oneOrMoreFiles := "object"
-		if len(m.receivedFiles) > 1 {
+		if len(m.receivedFiles) == 0 || len(m.receivedFiles) > 1 {
 			oneOrMoreFiles += "s"
 		}
-		finishedText := fmt.Sprintf("Received %d %s (%s compressed)", len(m.receivedFiles), oneOrMoreFiles, ui.ByteCountSI(m.payloadSize))
+		finishedText := fmt.Sprintf("Received %d %s (%s decompressed)", len(m.receivedFiles), oneOrMoreFiles, ui.ByteCountSI(m.decompressedPayloadSize))
 		return ui.PadText + ui.LogSeparator(m.width) +
 			ui.PadText + ui.InfoStyle(finishedText) + "\n\n" +
 			ui.PadText + m.transferProgress.View() + "\n\n" +
@@ -320,28 +388,57 @@ func listenReceiveCmd(msgs chan interface{}) tea.Cmd {
 	}
 }
 
-func decompressCmd(temp *os.File) tea.Cmd {
+func (m *model) listenOverwritePromptRequestsCmd() tea.Cmd {
+	return func() tea.Msg {
+		return <-m.overwritePromptRequests
+	}
+}
+
+func (m *model) decompressCmd(temp *os.File) tea.Cmd {
 	return func() tea.Msg {
-		// reset file position for reading
+		// Reset file position for reading.
 		_, err := temp.Seek(0, 0)
 		if err != nil {
 			return ui.ErrorMsg(err)
 		}
 
-		filenames, decompressedSize, err := file.DecompressAndUnarchiveBytes(temp)
+		// promptFunc is a no-op if we allow overwriting files without prompts.
+		promptFunc := func(fileName string) (bool, error) { return true, nil }
+		if viper.GetBool("prompt_overwrite_files") {
+			promptFunc = func(fileName string) (bool, error) {
+				m.overwritePromptRequests <- overwritePromptRequestMsg{fileName}
+				overwritePromptResponse := <-m.overwritePromptResponses
+				return overwritePromptResponse.shouldOverwrite, nil
+			}
+		}
+
+		fileNames, size, err := file.UnpackFiles(temp, promptFunc)
 		if err != nil {
 			return ui.ErrorMsg(err)
 		}
-		return decompressionDoneMsg{filenames: filenames, decompressedPayloadSize: decompressedSize}
+
+		return decompressionDoneMsg{fileNames, size}
 	}
 }
 
 // -------------------- HELPER METHODS -------------------------
 
+func (m *model) newOverwritePrompt(fileName string) tea.Cmd {
+	prompt := confirmation.New(fmt.Sprintf("Overwrite file '%s'?", fileName), confirmation.Yes)
+	m.overwritePrompt = *confirmation.NewModel(prompt)
+	m.overwritePrompt.MaxWidth = m.width
+	m.overwritePrompt.WrapMode = promptkit.HardWrap
+	m.overwritePrompt.Template = confirmation.TemplateYN
+	m.overwritePrompt.ResultTemplate = confirmation.ResultTemplateYN
+	m.overwritePrompt.KeyMap.Abort = []string{}
+	m.overwritePrompt.KeyMap.Toggle = []string{}
+	return m.overwritePrompt.Init()
+}
+
 func (m *model) resetSpinner() {
 	m.spinner = spinner.New()
 	m.spinner.Style = lipgloss.NewStyle().Foreground(lipgloss.Color(ui.ELEMENT_COLOR))
-	if m.state == showEstablishing {
+	if m.state == showEstablishing || m.state == showOverwritePrompt {
 		m.spinner.Spinner = ui.WaitingSpinner
 	}
 	if m.state == showDecompressing {
diff --git a/ui/sender/sender.go b/ui/sender/sender.go
index 656a484..8521dba 100644
--- a/ui/sender/sender.go
+++ b/ui/sender/sender.go
@@ -8,6 +8,7 @@ import (
 	"strings"
 	"time"
 
+	"github.com/SpatiumPortae/portal/internal/config"
 	"github.com/SpatiumPortae/portal/internal/conn"
 	"github.com/SpatiumPortae/portal/internal/file"
 	"github.com/SpatiumPortae/portal/internal/semver"
@@ -24,6 +25,7 @@ import (
 	tea "github.com/charmbracelet/bubbletea"
 	"github.com/charmbracelet/lipgloss"
 	"github.com/pkg/errors"
+	"github.com/spf13/viper"
 	"golang.org/x/exp/slices"
 )
 
@@ -250,7 +252,7 @@ func (m model) Update(msg tea.Msg) (tea.Model, tea.Cmd) {
 		case key.Matches(msg, m.keys.Quit):
 			return m, tea.Quit
 		case key.Matches(msg, m.keys.CopyPassword):
-			err := clipboard.WriteAll(fmt.Sprintf("portal receive %s", m.password))
+			err := clipboard.WriteAll(m.copyReceiverCommand())
 			if err != nil {
 				return m, ui.ErrorCmd(errors.New("Failed to copy password to clipboard"))
 			} else {
@@ -319,7 +321,7 @@ func (m model) View() string {
 		return ui.PadText + ui.LogSeparator(m.width) +
 			ui.PadText + ui.InfoStyle(statusText) + "\n\n" +
 			ui.PadText + ui.InfoStyle("On the receiving end, run:") + "\n" +
-			ui.PadText + ui.InfoStyle(fmt.Sprintf("portal receive %s", m.password)) + "\n\n" +
+			ui.PadText + ui.InfoStyle(m.copyReceiverCommand()) + "\n\n" +
 			m.fileTable.View() +
 			ui.PadText + m.help.View(m.keys) + "\n\n"
 
@@ -403,7 +405,12 @@ func readFilesCmd(paths []string) tea.Cmd {
 // provided files.
 func compressFilesCmd(files []*os.File) tea.Cmd {
 	return func() tea.Msg {
-		tar, size, err := file.ArchiveAndCompressFiles(files)
+		defer func() {
+			for _, f := range files {
+				f.Close()
+			}
+		}()
+		tar, size, err := file.PackFiles(files)
 		if err != nil {
 			return ui.ErrorMsg(err)
 		}
@@ -429,7 +436,7 @@ func listenTransferCmd(msgs chan interface{}) tea.Cmd {
 	}
 }
 
-// -------------------- HELPER METHODS -------------------------
+// -------------------------------------------------- Helper Functions -------------------------------------------------
 
 func (m *model) resetSpinner() {
 	m.spinner = spinner.New()
@@ -443,3 +450,19 @@ func (m *model) resetSpinner() {
 		m.spinner.Spinner = ui.TransferSpinner
 	}
 }
+
+func (m *model) copyReceiverCommand() string {
+	var builder strings.Builder
+	builder.WriteString("portal receive ")
+	builder.WriteString(m.password)
+
+	relayAddrKey := "relay"
+	if !config.IsDefault(relayAddrKey) {
+		builder.WriteRune(' ')
+		builder.WriteString(fmt.Sprintf("--%s", relayAddrKey))
+		builder.WriteRune(' ')
+		builder.WriteString(viper.GetString(relayAddrKey))
+	}
+
+	return builder.String()
+}