diff --git a/cmd/gotosocial/admincommands.go b/cmd/gotosocial/admincommands.go
index 5d505fe77..a70693b2c 100644
--- a/cmd/gotosocial/admincommands.go
+++ b/cmd/gotosocial/admincommands.go
@@ -25,7 +25,7 @@ import (
 	"github.com/urfave/cli/v2"
 )
 
-func adminCommands() []*cli.Command {
+func adminCommands(allFlags []cli.Flag) []*cli.Command {
 	return []*cli.Command{
 		{
 			Name:  "admin",
@@ -56,7 +56,7 @@ func adminCommands() []*cli.Command {
 								},
 							},
 							Action: func(c *cli.Context) error {
-								return runAction(c, account.Create)
+								return runAction(c, allFlags, account.Create)
 							},
 						},
 						{
@@ -70,7 +70,7 @@ func adminCommands() []*cli.Command {
 								},
 							},
 							Action: func(c *cli.Context) error {
-								return runAction(c, account.Confirm)
+								return runAction(c, allFlags, account.Confirm)
 							},
 						},
 						{
@@ -84,7 +84,7 @@ func adminCommands() []*cli.Command {
 								},
 							},
 							Action: func(c *cli.Context) error {
-								return runAction(c, account.Promote)
+								return runAction(c, allFlags, account.Promote)
 							},
 						},
 						{
@@ -98,7 +98,7 @@ func adminCommands() []*cli.Command {
 								},
 							},
 							Action: func(c *cli.Context) error {
-								return runAction(c, account.Demote)
+								return runAction(c, allFlags, account.Demote)
 							},
 						},
 						{
@@ -112,7 +112,7 @@ func adminCommands() []*cli.Command {
 								},
 							},
 							Action: func(c *cli.Context) error {
-								return runAction(c, account.Disable)
+								return runAction(c, allFlags, account.Disable)
 							},
 						},
 						{
@@ -126,7 +126,7 @@ func adminCommands() []*cli.Command {
 								},
 							},
 							Action: func(c *cli.Context) error {
-								return runAction(c, account.Suspend)
+								return runAction(c, allFlags, account.Suspend)
 							},
 						},
 						{
@@ -145,7 +145,7 @@ func adminCommands() []*cli.Command {
 								},
 							},
 							Action: func(c *cli.Context) error {
-								return runAction(c, account.Password)
+								return runAction(c, allFlags, account.Password)
 							},
 						},
 					},
@@ -161,7 +161,7 @@ func adminCommands() []*cli.Command {
 						},
 					},
 					Action: func(c *cli.Context) error {
-						return runAction(c, trans.Export)
+						return runAction(c, allFlags, trans.Export)
 					},
 				},
 				{
@@ -175,7 +175,7 @@ func adminCommands() []*cli.Command {
 						},
 					},
 					Action: func(c *cli.Context) error {
-						return runAction(c, trans.Import)
+						return runAction(c, allFlags, trans.Import)
 					},
 				},
 			},
diff --git a/cmd/gotosocial/commands.go b/cmd/gotosocial/commands.go
index 0c16d1fb5..9b61a66ec 100644
--- a/cmd/gotosocial/commands.go
+++ b/cmd/gotosocial/commands.go
@@ -22,12 +22,12 @@ import (
 	"github.com/urfave/cli/v2"
 )
 
-func getCommands() []*cli.Command {
+func getCommands(allFlags []cli.Flag) []*cli.Command {
 	commands := []*cli.Command{}
 	commandSets := [][]*cli.Command{
-		serverCommands(),
-		adminCommands(),
-		testrigCommands(),
+		serverCommands(allFlags),
+		adminCommands(allFlags),
+		testrigCommands(allFlags),
 	}
 	for _, cs := range commandSets {
 		commands = append(commands, cs...)
diff --git a/cmd/gotosocial/main.go b/cmd/gotosocial/main.go
index 3d41e0fda..87c44487c 100644
--- a/cmd/gotosocial/main.go
+++ b/cmd/gotosocial/main.go
@@ -42,11 +42,12 @@ func main() {
 		v = Version + " " + Commit[:7]
 	}
 
+	flagsSlice := getFlags()
 	app := &cli.App{
 		Version:  v,
 		Usage:    "a fediverse social media server",
-		Flags:    getFlags(),
-		Commands: getCommands(),
+		Flags:    flagsSlice,
+		Commands: getCommands(flagsSlice),
 	}
 
 	if err := app.Run(os.Args); err != nil {
diff --git a/cmd/gotosocial/runaction.go b/cmd/gotosocial/runaction.go
index c8af9ddbe..96c4edaf6 100644
--- a/cmd/gotosocial/runaction.go
+++ b/cmd/gotosocial/runaction.go
@@ -27,17 +27,48 @@ import (
 	"github.com/urfave/cli/v2"
 )
 
+type MonkeyPatchedCLIContext struct {
+	CLIContext *cli.Context
+	AllFlags   []cli.Flag
+}
+
+func (f MonkeyPatchedCLIContext) Bool(k string) bool            { return f.CLIContext.Bool(k) }
+func (f MonkeyPatchedCLIContext) String(k string) string        { return f.CLIContext.String(k) }
+func (f MonkeyPatchedCLIContext) StringSlice(k string) []string { return f.CLIContext.StringSlice(k) }
+func (f MonkeyPatchedCLIContext) Int(k string) int              { return f.CLIContext.Int(k) }
+func (f MonkeyPatchedCLIContext) IsSet(k string) bool {
+	for _, flag := range f.AllFlags {
+		flagNames := flag.Names()
+		for _, name := range flagNames {
+			if name == k {
+				return flag.IsSet()
+			}
+		}
+
+	}
+	return false
+}
+
 // runAction builds up the config and logger necessary for any
 // gotosocial action, and then executes the action.
-func runAction(c *cli.Context, a cliactions.GTSAction) error {
+func runAction(c *cli.Context, allFlags []cli.Flag, a cliactions.GTSAction) error {
 
 	// create a new *config.Config based on the config path provided...
 	conf, err := config.FromFile(c.String(config.GetFlagNames().ConfigPath))
 	if err != nil {
 		return fmt.Errorf("error creating config: %s", err)
 	}
+
 	// ... and the flags set on the *cli.Context by urfave
-	if err := conf.ParseCLIFlags(c, c.App.Version); err != nil {
+	//
+	// The IsSet function on the cli.Context object `c` here appears to have some issues right now, it always returns false in my tests.
+	// However we can re-create the behaviour we want by simply referencing the flag objects we created previously
+	// https://picopublish.sequentialread.com/files/chatlog_2021_11_18.txt
+	monkeyPatchedCLIContext := MonkeyPatchedCLIContext{
+		CLIContext: c,
+		AllFlags:   allFlags,
+	}
+	if err := conf.ParseCLIFlags(monkeyPatchedCLIContext, c.App.Version); err != nil {
 		return fmt.Errorf("error parsing config: %s", err)
 	}
 
diff --git a/cmd/gotosocial/servercommands.go b/cmd/gotosocial/servercommands.go
index 7a1692b79..fb6574216 100644
--- a/cmd/gotosocial/servercommands.go
+++ b/cmd/gotosocial/servercommands.go
@@ -23,7 +23,7 @@ import (
 	"github.com/urfave/cli/v2"
 )
 
-func serverCommands() []*cli.Command {
+func serverCommands(allFlags []cli.Flag) []*cli.Command {
 	return []*cli.Command{
 		{
 			Name:  "server",
@@ -33,7 +33,7 @@ func serverCommands() []*cli.Command {
 					Name:  "start",
 					Usage: "start the gotosocial server",
 					Action: func(c *cli.Context) error {
-						return runAction(c, server.Start)
+						return runAction(c, allFlags, server.Start)
 					},
 				},
 			},
diff --git a/cmd/gotosocial/testrigcommands.go b/cmd/gotosocial/testrigcommands.go
index 9b9aa3806..aabe04267 100644
--- a/cmd/gotosocial/testrigcommands.go
+++ b/cmd/gotosocial/testrigcommands.go
@@ -23,7 +23,7 @@ import (
 	"github.com/urfave/cli/v2"
 )
 
-func testrigCommands() []*cli.Command {
+func testrigCommands(allFlags []cli.Flag) []*cli.Command {
 	return []*cli.Command{
 		{
 			Name:  "testrig",
@@ -33,7 +33,7 @@ func testrigCommands() []*cli.Command {
 					Name:  "start",
 					Usage: "start the gotosocial testrig",
 					Action: func(c *cli.Context) error {
-						return runAction(c, testrig.Start)
+						return runAction(c, allFlags, testrig.Start)
 					},
 				},
 			},
diff --git a/internal/api/client/auth/auth_test.go b/internal/api/client/auth/auth_test.go
index ca606e8f2..ae58ffbbb 100644
--- a/internal/api/client/auth/auth_test.go
+++ b/internal/api/client/auth/auth_test.go
@@ -47,7 +47,7 @@ type AuthTestSuite struct {
 
 // SetupSuite sets some variables on the suite that we can use as consts (more or less) throughout
 func (suite *AuthTestSuite) SetupSuite() {
-	c := config.Empty()
+	c := config.Default()
 	// we're running on localhost without https so set the protocol to http
 	c.Protocol = "http"
 	// just for testing
diff --git a/internal/config/config.go b/internal/config/config.go
index 9daeba0f0..eb9e6385b 100644
--- a/internal/config/config.go
+++ b/internal/config/config.go
@@ -83,24 +83,7 @@ func FromFile(path string) (*Config, error) {
 		}
 		return c, nil
 	}
-	return Empty(), nil
-}
-
-// Empty just returns a new empty config
-func Empty() *Config {
-	return &Config{
-		DBConfig:          &DBConfig{},
-		TemplateConfig:    &TemplateConfig{},
-		AccountsConfig:    &AccountsConfig{},
-		MediaConfig:       &MediaConfig{},
-		StorageConfig:     &StorageConfig{},
-		StatusesConfig:    &StatusesConfig{},
-		LetsEncryptConfig: &LetsEncryptConfig{},
-		OIDCConfig:        &OIDCConfig{},
-		SMTPConfig:        &SMTPConfig{},
-		AccountCLIFlags:   make(map[string]string),
-		ExportCLIFlags:    make(map[string]string),
-	}
+	return Default(), nil
 }
 
 // loadFromFile takes a path to a yaml file and attempts to load a Config object from it
@@ -110,7 +93,7 @@ func loadFromFile(path string) (*Config, error) {
 		return nil, fmt.Errorf("could not read file at path %s: %s", path, err)
 	}
 
-	config := Empty()
+	config := Default()
 	if err := yaml.Unmarshal(bytes, config); err != nil {
 		return nil, fmt.Errorf("could not unmarshal file at path %s: %s", path, err)
 	}
@@ -131,87 +114,87 @@ func (c *Config) ParseCLIFlags(f KeyedFlags, version string) error {
 	//    as a command-line argument or an env variable, which takes priority.
 
 	// general flags
-	if c.LogLevel == "" || f.IsSet(fn.LogLevel) {
+	if f.IsSet(fn.LogLevel) {
 		c.LogLevel = f.String(fn.LogLevel)
 	}
 
-	if c.ApplicationName == "" || f.IsSet(fn.ApplicationName) {
+	if f.IsSet(fn.ApplicationName) {
 		c.ApplicationName = f.String(fn.ApplicationName)
 	}
 
-	if c.Host == "" || f.IsSet(fn.Host) {
+	if f.IsSet(fn.Host) {
 		c.Host = f.String(fn.Host)
 	}
 	if c.Host == "" {
 		return errors.New("host was not set")
 	}
 
-	if c.AccountDomain == "" || f.IsSet(fn.AccountDomain) {
+	if f.IsSet(fn.AccountDomain) {
 		c.AccountDomain = f.String(fn.AccountDomain)
 	}
 	if c.AccountDomain == "" {
 		c.AccountDomain = c.Host // default to whatever the host is, if this is empty
 	}
 
-	if c.Protocol == "" || f.IsSet(fn.Protocol) {
+	if f.IsSet(fn.Protocol) {
 		c.Protocol = f.String(fn.Protocol)
 	}
 	if c.Protocol == "" {
 		return errors.New("protocol was not set")
 	}
 
-	if c.BindAddress == "" || f.IsSet(fn.BindAddress) {
+	if f.IsSet(fn.BindAddress) {
 		c.BindAddress = f.String(fn.BindAddress)
 	}
 
-	if c.Port == 0 || f.IsSet(fn.Port) {
+	if f.IsSet(fn.Port) {
 		c.Port = f.Int(fn.Port)
 	}
 
-	if len(c.TrustedProxies) == 0 || f.IsSet(fn.TrustedProxies) {
+	if f.IsSet(fn.TrustedProxies) {
 		c.TrustedProxies = f.StringSlice(fn.TrustedProxies)
 	}
 
 	// db flags
-	if c.DBConfig.Type == "" || f.IsSet(fn.DbType) {
+	if f.IsSet(fn.DbType) {
 		c.DBConfig.Type = f.String(fn.DbType)
 	}
 
-	if c.DBConfig.Address == "" || f.IsSet(fn.DbAddress) {
+	if f.IsSet(fn.DbAddress) {
 		c.DBConfig.Address = f.String(fn.DbAddress)
 	}
 
-	if c.DBConfig.Port == 0 || f.IsSet(fn.DbPort) {
+	if f.IsSet(fn.DbPort) {
 		c.DBConfig.Port = f.Int(fn.DbPort)
 	}
 
-	if c.DBConfig.User == "" || f.IsSet(fn.DbUser) {
+	if f.IsSet(fn.DbUser) {
 		c.DBConfig.User = f.String(fn.DbUser)
 	}
 
-	if c.DBConfig.Password == "" || f.IsSet(fn.DbPassword) {
+	if f.IsSet(fn.DbPassword) {
 		c.DBConfig.Password = f.String(fn.DbPassword)
 	}
 
-	if c.DBConfig.Database == "" || f.IsSet(fn.DbDatabase) {
+	if f.IsSet(fn.DbDatabase) {
 		c.DBConfig.Database = f.String(fn.DbDatabase)
 	}
 
-	if c.DBConfig.TLSMode == DBTLSModeUnset || f.IsSet(fn.DbTLSMode) {
+	if f.IsSet(fn.DbTLSMode) {
 		c.DBConfig.TLSMode = DBTLSMode(f.String(fn.DbTLSMode))
 	}
 
-	if c.DBConfig.TLSCACert == "" || f.IsSet(fn.DbTLSCACert) {
+	if f.IsSet(fn.DbTLSCACert) {
 		c.DBConfig.TLSCACert = f.String(fn.DbTLSCACert)
 	}
 
 	// template flags
-	if c.TemplateConfig.BaseDir == "" || f.IsSet(fn.TemplateBaseDir) {
+	if f.IsSet(fn.TemplateBaseDir) {
 		c.TemplateConfig.BaseDir = f.String(fn.TemplateBaseDir)
 	}
 
 	// template flags
-	if c.TemplateConfig.AssetBaseDir == "" || f.IsSet(fn.AssetBaseDir) {
+	if f.IsSet(fn.AssetBaseDir) {
 		c.TemplateConfig.AssetBaseDir = f.String(fn.AssetBaseDir)
 	}
 
@@ -225,57 +208,57 @@ func (c *Config) ParseCLIFlags(f KeyedFlags, version string) error {
 	}
 
 	// media flags
-	if c.MediaConfig.MaxImageSize == 0 || f.IsSet(fn.MediaMaxImageSize) {
+	if f.IsSet(fn.MediaMaxImageSize) {
 		c.MediaConfig.MaxImageSize = f.Int(fn.MediaMaxImageSize)
 	}
 
-	if c.MediaConfig.MaxVideoSize == 0 || f.IsSet(fn.MediaMaxVideoSize) {
+	if f.IsSet(fn.MediaMaxVideoSize) {
 		c.MediaConfig.MaxVideoSize = f.Int(fn.MediaMaxVideoSize)
 	}
 
-	if c.MediaConfig.MinDescriptionChars == 0 || f.IsSet(fn.MediaMinDescriptionChars) {
+	if f.IsSet(fn.MediaMinDescriptionChars) {
 		c.MediaConfig.MinDescriptionChars = f.Int(fn.MediaMinDescriptionChars)
 	}
 
-	if c.MediaConfig.MaxDescriptionChars == 0 || f.IsSet(fn.MediaMaxDescriptionChars) {
+	if f.IsSet(fn.MediaMaxDescriptionChars) {
 		c.MediaConfig.MaxDescriptionChars = f.Int(fn.MediaMaxDescriptionChars)
 	}
 
 	// storage flags
-	if c.StorageConfig.Backend == "" || f.IsSet(fn.StorageBackend) {
+	if f.IsSet(fn.StorageBackend) {
 		c.StorageConfig.Backend = f.String(fn.StorageBackend)
 	}
 
-	if c.StorageConfig.BasePath == "" || f.IsSet(fn.StorageBasePath) {
+	if f.IsSet(fn.StorageBasePath) {
 		c.StorageConfig.BasePath = f.String(fn.StorageBasePath)
 	}
 
-	if c.StorageConfig.ServeProtocol == "" || f.IsSet(fn.StorageServeProtocol) {
+	if f.IsSet(fn.StorageServeProtocol) {
 		c.StorageConfig.ServeProtocol = f.String(fn.StorageServeProtocol)
 	}
 
-	if c.StorageConfig.ServeHost == "" || f.IsSet(fn.StorageServeHost) {
+	if f.IsSet(fn.StorageServeHost) {
 		c.StorageConfig.ServeHost = f.String(fn.StorageServeHost)
 	}
 
-	if c.StorageConfig.ServeBasePath == "" || f.IsSet(fn.StorageServeBasePath) {
+	if f.IsSet(fn.StorageServeBasePath) {
 		c.StorageConfig.ServeBasePath = f.String(fn.StorageServeBasePath)
 	}
 
 	// statuses flags
-	if c.StatusesConfig.MaxChars == 0 || f.IsSet(fn.StatusesMaxChars) {
+	if f.IsSet(fn.StatusesMaxChars) {
 		c.StatusesConfig.MaxChars = f.Int(fn.StatusesMaxChars)
 	}
-	if c.StatusesConfig.CWMaxChars == 0 || f.IsSet(fn.StatusesCWMaxChars) {
+	if f.IsSet(fn.StatusesCWMaxChars) {
 		c.StatusesConfig.CWMaxChars = f.Int(fn.StatusesCWMaxChars)
 	}
-	if c.StatusesConfig.PollMaxOptions == 0 || f.IsSet(fn.StatusesPollMaxOptions) {
+	if f.IsSet(fn.StatusesPollMaxOptions) {
 		c.StatusesConfig.PollMaxOptions = f.Int(fn.StatusesPollMaxOptions)
 	}
-	if c.StatusesConfig.PollOptionMaxChars == 0 || f.IsSet(fn.StatusesPollOptionMaxChars) {
+	if f.IsSet(fn.StatusesPollOptionMaxChars) {
 		c.StatusesConfig.PollOptionMaxChars = f.Int(fn.StatusesPollOptionMaxChars)
 	}
-	if c.StatusesConfig.MaxMediaFiles == 0 || f.IsSet(fn.StatusesMaxMediaFiles) {
+	if f.IsSet(fn.StatusesMaxMediaFiles) {
 		c.StatusesConfig.MaxMediaFiles = f.Int(fn.StatusesMaxMediaFiles)
 	}
 
@@ -284,15 +267,15 @@ func (c *Config) ParseCLIFlags(f KeyedFlags, version string) error {
 		c.LetsEncryptConfig.Enabled = f.Bool(fn.LetsEncryptEnabled)
 	}
 
-	if c.LetsEncryptConfig.Port == 0 || f.IsSet(fn.LetsEncryptPort) {
+	if f.IsSet(fn.LetsEncryptPort) {
 		c.LetsEncryptConfig.Port = f.Int(fn.LetsEncryptPort)
 	}
 
-	if c.LetsEncryptConfig.CertDir == "" || f.IsSet(fn.LetsEncryptCertDir) {
+	if f.IsSet(fn.LetsEncryptCertDir) {
 		c.LetsEncryptConfig.CertDir = f.String(fn.LetsEncryptCertDir)
 	}
 
-	if c.LetsEncryptConfig.EmailAddress == "" || f.IsSet(fn.LetsEncryptEmailAddress) {
+	if f.IsSet(fn.LetsEncryptEmailAddress) {
 		c.LetsEncryptConfig.EmailAddress = f.String(fn.LetsEncryptEmailAddress)
 	}
 
@@ -301,7 +284,7 @@ func (c *Config) ParseCLIFlags(f KeyedFlags, version string) error {
 		c.OIDCConfig.Enabled = f.Bool(fn.OIDCEnabled)
 	}
 
-	if c.OIDCConfig.IDPName == "" || f.IsSet(fn.OIDCIdpName) {
+	if f.IsSet(fn.OIDCIdpName) {
 		c.OIDCConfig.IDPName = f.String(fn.OIDCIdpName)
 	}
 
@@ -309,40 +292,40 @@ func (c *Config) ParseCLIFlags(f KeyedFlags, version string) error {
 		c.OIDCConfig.SkipVerification = f.Bool(fn.OIDCSkipVerification)
 	}
 
-	if c.OIDCConfig.Issuer == "" || f.IsSet(fn.OIDCIssuer) {
+	if f.IsSet(fn.OIDCIssuer) {
 		c.OIDCConfig.Issuer = f.String(fn.OIDCIssuer)
 	}
 
-	if c.OIDCConfig.ClientID == "" || f.IsSet(fn.OIDCClientID) {
+	if f.IsSet(fn.OIDCClientID) {
 		c.OIDCConfig.ClientID = f.String(fn.OIDCClientID)
 	}
 
-	if c.OIDCConfig.ClientSecret == "" || f.IsSet(fn.OIDCClientSecret) {
+	if f.IsSet(fn.OIDCClientSecret) {
 		c.OIDCConfig.ClientSecret = f.String(fn.OIDCClientSecret)
 	}
 
-	if len(c.OIDCConfig.Scopes) == 0 || f.IsSet(fn.OIDCScopes) {
+	if f.IsSet(fn.OIDCScopes) {
 		c.OIDCConfig.Scopes = f.StringSlice(fn.OIDCScopes)
 	}
 
 	// smtp flags
-	if c.SMTPConfig.Host == "" || f.IsSet(fn.SMTPHost) {
+	if f.IsSet(fn.SMTPHost) {
 		c.SMTPConfig.Host = f.String(fn.SMTPHost)
 	}
 
-	if c.SMTPConfig.Port == 0 || f.IsSet(fn.SMTPPort) {
+	if f.IsSet(fn.SMTPPort) {
 		c.SMTPConfig.Port = f.Int(fn.SMTPPort)
 	}
 
-	if c.SMTPConfig.Username == "" || f.IsSet(fn.SMTPUsername) {
+	if f.IsSet(fn.SMTPUsername) {
 		c.SMTPConfig.Username = f.String(fn.SMTPUsername)
 	}
 
-	if c.SMTPConfig.Password == "" || f.IsSet(fn.SMTPPassword) {
+	if f.IsSet(fn.SMTPPassword) {
 		c.SMTPConfig.Password = f.String(fn.SMTPPassword)
 	}
 
-	if c.SMTPConfig.From == "" || f.IsSet(fn.SMTPFrom) {
+	if f.IsSet(fn.SMTPFrom) {
 		c.SMTPConfig.From = f.String(fn.SMTPFrom)
 	}
 
diff --git a/internal/config/default.go b/internal/config/default.go
index 996033ae4..6e8f63177 100644
--- a/internal/config/default.go
+++ b/internal/config/default.go
@@ -150,6 +150,8 @@ func Default() *Config {
 			Password: defaults.SMTPPassword,
 			From:     defaults.SMTPFrom,
 		},
+		AccountCLIFlags: make(map[string]string),
+		ExportCLIFlags:  make(map[string]string),
 	}
 }