diff --git a/cmd/fleetctl/api.go b/cmd/fleetctl/api.go
index 91460ea19a..9c4bd9a2c9 100644
--- a/cmd/fleetctl/api.go
+++ b/cmd/fleetctl/api.go
@@ -6,7 +6,7 @@ import (
 
 	"github.com/fleetdm/fleet/server/service"
 	"github.com/pkg/errors"
-	"github.com/urfave/cli"
+	"github.com/urfave/cli/v2"
 )
 
 func unauthenticatedClientFromCLI(c *cli.Context) (*service.Client, error) {
diff --git a/cmd/fleetctl/apply.go b/cmd/fleetctl/apply.go
index 92c8378226..2f49b6f388 100644
--- a/cmd/fleetctl/apply.go
+++ b/cmd/fleetctl/apply.go
@@ -10,7 +10,7 @@ import (
 	"github.com/fleetdm/fleet/server/kolide"
 	"github.com/ghodss/yaml"
 	"github.com/pkg/errors"
-	"github.com/urfave/cli"
+	"github.com/urfave/cli/v2"
 )
 
 var (
@@ -114,18 +114,18 @@ func specGroupFromBytes(b []byte) (*specGroup, error) {
 	return specs, nil
 }
 
-func applyCommand() cli.Command {
+func applyCommand() *cli.Command {
 	var (
 		flFilename string
 	)
-	return cli.Command{
+	return &cli.Command{
 		Name:      "apply",
 		Usage:     "Apply files to declaratively manage osquery configurations",
 		UsageText: `fleetctl apply [options]`,
 		Flags: []cli.Flag{
-			cli.StringFlag{
+			&cli.StringFlag{
 				Name:        "f",
-				EnvVar:      "FILENAME",
+				EnvVars:     []string{"FILENAME"},
 				Value:       "",
 				Destination: &flFilename,
 				Usage:       "A file to apply",
diff --git a/cmd/fleetctl/config.go b/cmd/fleetctl/config.go
index b756210353..014c5b30dc 100644
--- a/cmd/fleetctl/config.go
+++ b/cmd/fleetctl/config.go
@@ -9,7 +9,7 @@ import (
 
 	"github.com/ghodss/yaml"
 	"github.com/pkg/errors"
-	"github.com/urfave/cli"
+	"github.com/urfave/cli/v2"
 )
 
 const (
@@ -35,20 +35,20 @@ func configFlag() cli.Flag {
 		homeDir = "~"
 	}
 	defaultConfigPath := filepath.Join(homeDir, ".fleet", "config")
-	return cli.StringFlag{
-		Name:   "config",
-		Value:  defaultConfigPath,
-		EnvVar: "CONFIG",
-		Usage:  "Path to the fleetctl config file",
+	return &cli.StringFlag{
+		Name:    "config",
+		Value:   defaultConfigPath,
+		EnvVars: []string{"CONFIG"},
+		Usage:   "Path to the fleetctl config file",
 	}
 }
 
 func contextFlag() cli.Flag {
-	return cli.StringFlag{
-		Name:   "context",
-		Value:  "default",
-		EnvVar: "CONTEXT",
-		Usage:  "Name of fleetctl config context to use",
+	return &cli.StringFlag{
+		Name:    "context",
+		Value:   "default",
+		EnvVars: []string{"CONTEXT"},
+		Usage:   "Name of fleetctl config context to use",
 	}
 }
 
@@ -175,7 +175,7 @@ func setConfigValue(configPath, context, key, value string) error {
 	return nil
 }
 
-func configSetCommand() cli.Command {
+func configSetCommand() *cli.Command {
 	var (
 		flAddress       string
 		flEmail         string
@@ -184,50 +184,50 @@ func configSetCommand() cli.Command {
 		flRootCA        string
 		flURLPrefix     string
 	)
-	return cli.Command{
+	return &cli.Command{
 		Name:      "set",
 		Usage:     "Set config options",
 		UsageText: `fleetctl config set [options]`,
 		Flags: []cli.Flag{
 			configFlag(),
 			contextFlag(),
-			cli.StringFlag{
+			&cli.StringFlag{
 				Name:        "address",
-				EnvVar:      "ADDRESS",
+				EnvVars:     []string{"ADDRESS"},
 				Value:       "",
 				Destination: &flAddress,
 				Usage:       "Address of the Fleet server",
 			},
-			cli.StringFlag{
+			&cli.StringFlag{
 				Name:        "email",
-				EnvVar:      "EMAIL",
+				EnvVars:     []string{"EMAIL"},
 				Value:       "",
 				Destination: &flEmail,
 				Usage:       "Email to use when connecting to the Fleet server",
 			},
-			cli.StringFlag{
+			&cli.StringFlag{
 				Name:        "token",
-				EnvVar:      "TOKEN",
+				EnvVars:     []string{"TOKEN"},
 				Value:       "",
 				Destination: &flToken,
 				Usage:       "Fleet API token",
 			},
-			cli.BoolFlag{
+			&cli.BoolFlag{
 				Name:        "tls-skip-verify",
-				EnvVar:      "INSECURE",
+				EnvVars:     []string{"INSECURE"},
 				Destination: &flTLSSkipVerify,
 				Usage:       "Skip TLS certificate validation",
 			},
-			cli.StringFlag{
+			&cli.StringFlag{
 				Name:        "rootca",
-				EnvVar:      "ROOTCA",
+				EnvVars:     []string{"ROOTCA"},
 				Value:       "",
 				Destination: &flRootCA,
 				Usage:       "Specify RootCA chain used to communicate with fleet",
 			},
-			cli.StringFlag{
+			&cli.StringFlag{
 				Name:        "url-prefix",
-				EnvVar:      "URL_PREFIX",
+				EnvVars:     []string{"URL_PREFIX"},
 				Value:       "",
 				Destination: &flURLPrefix,
 				Usage:       "Specify URL Prefix to use with Fleet server (copy from server configuration)",
@@ -295,8 +295,8 @@ func configSetCommand() cli.Command {
 	}
 }
 
-func configGetCommand() cli.Command {
-	return cli.Command{
+func configGetCommand() *cli.Command {
+	return &cli.Command{
 		Name:      "get",
 		Usage:     "Get a config option",
 		UsageText: `fleetctl config get [options]`,
@@ -305,11 +305,11 @@ func configGetCommand() cli.Command {
 			contextFlag(),
 		},
 		Action: func(c *cli.Context) error {
-			if len(c.Args()) != 1 {
+			if c.Args().Len() != 1 {
 				return cli.ShowCommandHelp(c, "get")
 			}
 
-			key := c.Args()[0]
+			key := c.Args().Get(0)
 
 			// validate key
 			switch key {
diff --git a/cmd/fleetctl/convert.go b/cmd/fleetctl/convert.go
index 1d059b8b23..16a43541e9 100644
--- a/cmd/fleetctl/convert.go
+++ b/cmd/fleetctl/convert.go
@@ -12,7 +12,7 @@ import (
 	"github.com/fleetdm/fleet/server/kolide"
 	"github.com/ghodss/yaml"
 	"github.com/pkg/errors"
-	"github.com/urfave/cli"
+	"github.com/urfave/cli/v2"
 )
 
 func specGroupFromPack(name string, inputPack kolide.PermissivePackContent) (*specGroup, error) {
@@ -66,20 +66,20 @@ func specGroupFromPack(name string, inputPack kolide.PermissivePackContent) (*sp
 	return specs, nil
 }
 
-func convertCommand() cli.Command {
+func convertCommand() *cli.Command {
 	var (
 		flFilename string
 	)
-	return cli.Command{
+	return &cli.Command{
 		Name:      "convert",
 		Usage:     "Convert osquery packs into decomposed fleet configs",
 		UsageText: `fleetctl convert [options]`,
 		Flags: []cli.Flag{
 			configFlag(),
 			contextFlag(),
-			cli.StringFlag{
+			&cli.StringFlag{
 				Name:        "f",
-				EnvVar:      "FILENAME",
+				EnvVars:     []string{"FILENAME"},
 				Value:       "",
 				Destination: &flFilename,
 				Usage:       "A file to apply",
diff --git a/cmd/fleetctl/debug.go b/cmd/fleetctl/debug.go
index 115a7325b6..52585c5054 100644
--- a/cmd/fleetctl/debug.go
+++ b/cmd/fleetctl/debug.go
@@ -10,11 +10,11 @@ import (
 	"time"
 
 	"github.com/pkg/errors"
-	"github.com/urfave/cli"
+	"github.com/urfave/cli/v2"
 )
 
-func debugCommand() cli.Command {
-	return cli.Command{
+func debugCommand() *cli.Command {
+	return &cli.Command{
 		Name:  "debug",
 		Usage: "Tools for debugging Fleet",
 		Flags: []cli.Flag{
@@ -22,7 +22,7 @@ func debugCommand() cli.Command {
 			contextFlag(),
 			debugFlag(),
 		},
-		Subcommands: []cli.Command{
+		Subcommands: []*cli.Command{
 			debugProfileCommand(),
 			debugCmdlineCommand(),
 			debugHeapCommand(),
@@ -46,8 +46,8 @@ func outfileName(name string) string {
 	return fmt.Sprintf("fleet-%s-%s", name, time.Now().Format(time.RFC3339))
 }
 
-func debugProfileCommand() cli.Command {
-	return cli.Command{
+func debugProfileCommand() *cli.Command {
+	return &cli.Command{
 		Name:      "profile",
 		Usage:     "Record a CPU profile from the Fleet server.",
 		UsageText: "Record a 30-second CPU profile. The output can be analyzed with go tool pprof.",
@@ -90,8 +90,8 @@ func joinCmdline(cmdline string) string {
 	return fmt.Sprintf("[%s]", strings.Join(tokens, ", "))
 }
 
-func debugCmdlineCommand() cli.Command {
-	return cli.Command{
+func debugCmdlineCommand() *cli.Command {
+	return &cli.Command{
 		Name:  "cmdline",
 		Usage: "Get the command line used to invoke the Fleet server.",
 		Flags: []cli.Flag{
@@ -127,9 +127,9 @@ func debugCmdlineCommand() cli.Command {
 	}
 }
 
-func debugHeapCommand() cli.Command {
+func debugHeapCommand() *cli.Command {
 	name := "heap"
-	return cli.Command{
+	return &cli.Command{
 		Name:      name,
 		Usage:     "Report the allocated memory in the Fleet server.",
 		UsageText: "Report the heap-allocated memory. The output can be analyzed with go tool pprof.",
@@ -164,9 +164,9 @@ func debugHeapCommand() cli.Command {
 	}
 }
 
-func debugGoroutineCommand() cli.Command {
+func debugGoroutineCommand() *cli.Command {
 	name := "goroutine"
-	return cli.Command{
+	return &cli.Command{
 		Name:      name,
 		Usage:     "Get stack traces of all goroutines (threads) in the Fleet server.",
 		UsageText: "Get stack traces of all current goroutines (threads). The output can be analyzed with go tool pprof.",
@@ -201,9 +201,9 @@ func debugGoroutineCommand() cli.Command {
 	}
 }
 
-func debugTraceCommand() cli.Command {
+func debugTraceCommand() *cli.Command {
 	name := "trace"
-	return cli.Command{
+	return &cli.Command{
 		Name:      name,
 		Usage:     "Record an execution trace on the Fleet server.",
 		UsageText: "Record a 1 second execution trace. The output can be analyzed with go tool trace.",
@@ -238,8 +238,8 @@ func debugTraceCommand() cli.Command {
 	}
 }
 
-func debugArchiveCommand() cli.Command {
-	return cli.Command{
+func debugArchiveCommand() *cli.Command {
+	return &cli.Command{
 		Name:  "archive",
 		Usage: "Create an archive with the entire suite of debug profiles.",
 		Flags: []cli.Flag{
diff --git a/cmd/fleetctl/delete.go b/cmd/fleetctl/delete.go
index d5718641dc..363ad06a9d 100644
--- a/cmd/fleetctl/delete.go
+++ b/cmd/fleetctl/delete.go
@@ -6,21 +6,21 @@ import (
 
 	"github.com/fleetdm/fleet/server/service"
 	"github.com/pkg/errors"
-	"github.com/urfave/cli"
+	"github.com/urfave/cli/v2"
 )
 
-func deleteCommand() cli.Command {
+func deleteCommand() *cli.Command {
 	var (
 		flFilename string
 	)
-	return cli.Command{
+	return &cli.Command{
 		Name:      "delete",
 		Usage:     "Specify files to declaratively batch delete osquery configurations",
 		UsageText: `fleetctl delete [options]`,
 		Flags: []cli.Flag{
-			cli.StringFlag{
+			&cli.StringFlag{
 				Name:        "f",
-				EnvVar:      "FILENAME",
+				EnvVars:     []string{"FILENAME"},
 				Value:       "",
 				Destination: &flFilename,
 				Usage:       "A file to apply",
diff --git a/cmd/fleetctl/flags.go b/cmd/fleetctl/flags.go
index 70acb87969..af1bca89d8 100644
--- a/cmd/fleetctl/flags.go
+++ b/cmd/fleetctl/flags.go
@@ -1,6 +1,6 @@
 package main
 
-import "github.com/urfave/cli"
+import "github.com/urfave/cli/v2"
 
 const (
 	outfileFlagName = "outfile"
@@ -8,11 +8,11 @@ const (
 )
 
 func outfileFlag() cli.Flag {
-	return cli.StringFlag{
-		Name:   outfileFlagName,
-		Value:  "",
-		EnvVar: "OUTFILE",
-		Usage:  "Path to output file",
+	return &cli.StringFlag{
+		Name:    outfileFlagName,
+		Value:   "",
+		EnvVars: []string{"OUTFILE"},
+		Usage:   "Path to output file",
 	}
 }
 
@@ -21,10 +21,10 @@ func getOutfile(c *cli.Context) string {
 }
 
 func debugFlag() cli.Flag {
-	return cli.BoolFlag{
-		Name:   debugFlagName,
-		EnvVar: "DEBUG",
-		Usage:  "Enable debug http request logging",
+	return &cli.BoolFlag{
+		Name:    debugFlagName,
+		EnvVars: []string{"DEBUG"},
+		Usage:   "Enable debug http request logging",
 	}
 }
 
diff --git a/cmd/fleetctl/fleetctl.go b/cmd/fleetctl/fleetctl.go
index 9b9110ca70..8c57f7ddb5 100644
--- a/cmd/fleetctl/fleetctl.go
+++ b/cmd/fleetctl/fleetctl.go
@@ -5,7 +5,7 @@ import (
 	"time"
 
 	"github.com/kolide/kit/version"
-	"github.com/urfave/cli"
+	"github.com/urfave/cli/v2"
 )
 
 const (
@@ -25,7 +25,7 @@ func main() {
 		version.PrintFull()
 	}
 
-	app.Commands = []cli.Command{
+	app.Commands = []*cli.Command{
 		applyCommand(),
 		deleteCommand(),
 		setupCommand(),
@@ -33,10 +33,10 @@ func main() {
 		logoutCommand(),
 		queryCommand(),
 		getCommand(),
-		cli.Command{
+		&cli.Command{
 			Name:  "config",
 			Usage: "Modify Fleet server connection settings",
-			Subcommands: []cli.Command{
+			Subcommands: []*cli.Command{
 				configSetCommand(),
 				configGetCommand(),
 			},
diff --git a/cmd/fleetctl/get.go b/cmd/fleetctl/get.go
index cb061946f9..a183115890 100644
--- a/cmd/fleetctl/get.go
+++ b/cmd/fleetctl/get.go
@@ -11,7 +11,7 @@ import (
 	"github.com/ghodss/yaml"
 	"github.com/olekukonko/tablewriter"
 	"github.com/pkg/errors"
-	"github.com/urfave/cli"
+	"github.com/urfave/cli/v2"
 )
 
 const (
@@ -34,15 +34,15 @@ func defaultTable() *tablewriter.Table {
 	return table
 }
 
-func yamlFlag() cli.BoolFlag {
-	return cli.BoolFlag{
+func yamlFlag() cli.Flag {
+	return &cli.BoolFlag{
 		Name:  yamlFlagName,
 		Usage: "Output in yaml format",
 	}
 }
 
-func jsonFlag() cli.BoolFlag {
-	return cli.BoolFlag{
+func jsonFlag() cli.Flag {
+	return &cli.BoolFlag{
 		Name:  jsonFlagName,
 		Usage: "Output in JSON format",
 	}
@@ -201,11 +201,11 @@ func printConfig(c *cli.Context, config *kolide.AppConfigPayload) error {
 	return err
 }
 
-func getCommand() cli.Command {
-	return cli.Command{
+func getCommand() *cli.Command {
+	return &cli.Command{
 		Name:  "get",
 		Usage: "Get/list resources",
-		Subcommands: []cli.Command{
+		Subcommands: []*cli.Command{
 			getQueriesCommand(),
 			getPacksCommand(),
 			getLabelsCommand(),
@@ -219,8 +219,8 @@ func getCommand() cli.Command {
 	}
 }
 
-func getQueriesCommand() cli.Command {
-	return cli.Command{
+func getQueriesCommand() *cli.Command {
+	return &cli.Command{
 		Name:    "queries",
 		Aliases: []string{"query", "q"},
 		Usage:   "List information about one or more queries",
@@ -292,13 +292,13 @@ func getQueriesCommand() cli.Command {
 	}
 }
 
-func getPacksCommand() cli.Command {
-	return cli.Command{
+func getPacksCommand() *cli.Command {
+	return &cli.Command{
 		Name:    "packs",
 		Aliases: []string{"pack", "p"},
 		Usage:   "List information about one or more packs",
 		Flags: []cli.Flag{
-			cli.BoolFlag{
+			&cli.BoolFlag{
 				Name:  withQueriesFlagName,
 				Usage: "Output queries included in pack(s) too",
 			},
@@ -412,8 +412,8 @@ func getPacksCommand() cli.Command {
 	}
 }
 
-func getLabelsCommand() cli.Command {
-	return cli.Command{
+func getLabelsCommand() *cli.Command {
+	return &cli.Command{
 		Name:    "labels",
 		Aliases: []string{"label", "l"},
 		Usage:   "List information about one or more labels",
@@ -484,8 +484,8 @@ func getLabelsCommand() cli.Command {
 	}
 }
 
-func getOptionsCommand() cli.Command {
-	return cli.Command{
+func getOptionsCommand() *cli.Command {
+	return &cli.Command{
 		Name:  "options",
 		Usage: "Retrieve the osquery configuration",
 		Flags: []cli.Flag{
@@ -516,8 +516,8 @@ func getOptionsCommand() cli.Command {
 	}
 }
 
-func getEnrollSecretCommand() cli.Command {
-	return cli.Command{
+func getEnrollSecretCommand() *cli.Command {
+	return &cli.Command{
 		Name:    "enroll_secret",
 		Aliases: []string{"enroll_secrets", "enroll-secret", "enroll-secrets"},
 		Usage:   "Retrieve the osquery enroll secrets",
@@ -549,8 +549,8 @@ func getEnrollSecretCommand() cli.Command {
 	}
 }
 
-func getAppConfigCommand() cli.Command {
-	return cli.Command{
+func getAppConfigCommand() *cli.Command {
+	return &cli.Command{
 		Name:  "config",
 		Usage: "Retrieve the Fleet configuration",
 		Flags: []cli.Flag{
@@ -581,8 +581,8 @@ func getAppConfigCommand() cli.Command {
 	}
 }
 
-func getHostsCommand() cli.Command {
-	return cli.Command{
+func getHostsCommand() *cli.Command {
+	return &cli.Command{
 		Name:    "hosts",
 		Aliases: []string{"host", "h"},
 		Usage:   "List information about one or more hosts",
@@ -656,12 +656,12 @@ func getHostsCommand() cli.Command {
 	}
 }
 
-func getCarvesCommand() cli.Command {
-	return cli.Command{
+func getCarvesCommand() *cli.Command {
+	return &cli.Command{
 		Name:  "carves",
 		Usage: "Retrieve the file carving sessions",
 		Flags: []cli.Flag{
-			cli.BoolFlag{
+			&cli.BoolFlag{
 				Name:  expiredFlagName,
 				Usage: "Include expired carves",
 			},
@@ -716,12 +716,12 @@ func getCarvesCommand() cli.Command {
 	}
 }
 
-func getCarveCommand() cli.Command {
-	return cli.Command{
+func getCarveCommand() *cli.Command {
+	return &cli.Command{
 		Name:  "carve",
 		Usage: "Retrieve details for a carve by ID",
 		Flags: []cli.Flag{
-			cli.BoolFlag{
+			&cli.BoolFlag{
 				Name:  stdoutFlagName,
 				Usage: "Print carve contents to stdout",
 			},
diff --git a/cmd/fleetctl/goquery.go b/cmd/fleetctl/goquery.go
index ed5880edc7..515eddfa7d 100644
--- a/cmd/fleetctl/goquery.go
+++ b/cmd/fleetctl/goquery.go
@@ -11,7 +11,7 @@ import (
 	"github.com/fleetdm/fleet/server/kolide"
 	"github.com/fleetdm/fleet/server/service"
 	"github.com/pkg/errors"
-	"github.com/urfave/cli"
+	"github.com/urfave/cli/v2"
 )
 
 type activeQuery struct {
@@ -110,8 +110,8 @@ func (c *goqueryClient) FetchResults(queryName string) (gqmodels.Rows, string, e
 	return res.results, res.status, nil
 }
 
-func goqueryCommand() cli.Command {
-	return cli.Command{
+func goqueryCommand() *cli.Command {
+	return &cli.Command{
 		Name:  "goquery",
 		Usage: "Start the goquery interface",
 		Flags: []cli.Flag{
diff --git a/cmd/fleetctl/login.go b/cmd/fleetctl/login.go
index 0c7582d1ac..7ff71e2c3b 100644
--- a/cmd/fleetctl/login.go
+++ b/cmd/fleetctl/login.go
@@ -6,16 +6,16 @@ import (
 
 	"github.com/fleetdm/fleet/server/service"
 	"github.com/pkg/errors"
-	"github.com/urfave/cli"
+	"github.com/urfave/cli/v2"
 	"golang.org/x/crypto/ssh/terminal"
 )
 
-func loginCommand() cli.Command {
+func loginCommand() *cli.Command {
 	var (
 		flEmail    string
 		flPassword string
 	)
-	return cli.Command{
+	return &cli.Command{
 		Name:  "login",
 		Usage: "Login to Fleet",
 		UsageText: `
@@ -24,16 +24,16 @@ fleetctl login [options]
 Interactively prompts for email and password if not specified in the flags or environment variables.
 `,
 		Flags: []cli.Flag{
-			cli.StringFlag{
+			&cli.StringFlag{
 				Name:        "email",
-				EnvVar:      "EMAIL",
+				EnvVars:     []string{"EMAIL"},
 				Value:       "",
 				Destination: &flEmail,
 				Usage:       "Email or username to use to log in",
 			},
-			cli.StringFlag{
+			&cli.StringFlag{
 				Name:        "password",
-				EnvVar:      "PASSWORD",
+				EnvVars:     []string{"PASSWORD"},
 				Value:       "",
 				Destination: &flPassword,
 				Usage:       "Password to use to log in (recommended to use interactive entry)",
diff --git a/cmd/fleetctl/logout.go b/cmd/fleetctl/logout.go
index 8df90ab710..142409e899 100644
--- a/cmd/fleetctl/logout.go
+++ b/cmd/fleetctl/logout.go
@@ -4,11 +4,11 @@ import (
 	"fmt"
 
 	"github.com/pkg/errors"
-	"github.com/urfave/cli"
+	"github.com/urfave/cli/v2"
 )
 
-func logoutCommand() cli.Command {
-	return cli.Command{
+func logoutCommand() *cli.Command {
+	return &cli.Command{
 		Name:      "logout",
 		Usage:     "Log out of Fleet",
 		UsageText: `fleetctl logout [options]`,
diff --git a/cmd/fleetctl/preview.go b/cmd/fleetctl/preview.go
index ec71696be1..a6c5d45dc9 100644
--- a/cmd/fleetctl/preview.go
+++ b/cmd/fleetctl/preview.go
@@ -17,21 +17,21 @@ import (
 	"github.com/cenkalti/backoff/v4"
 	"github.com/fleetdm/fleet/server/service"
 	"github.com/pkg/errors"
-	"github.com/urfave/cli"
+	"github.com/urfave/cli/v2"
 )
 
 const (
 	downloadUrl = "https://github.com/fleetdm/osquery-in-a-box/archive/master.zip"
 )
 
-func previewCommand() cli.Command {
-	return cli.Command{
+func previewCommand() *cli.Command {
+	return &cli.Command{
 		Name:  "preview",
 		Usage: "Set up a preview deployment of the Fleet server",
 		UsageText: `Set up a preview deployment of the Fleet server using Docker and docker-compose. Docker tools must be available in the environment.
 
 This command will create a directory fleet-preview in the current working directory. Configurations can be modified in that directory.`,
-		Subcommands: []cli.Command{},
+		Subcommands: []*cli.Command{},
 		Flags: []cli.Flag{
 			configFlag(),
 			contextFlag(),
diff --git a/cmd/fleetctl/query.go b/cmd/fleetctl/query.go
index e2c0933b33..8fa9116979 100644
--- a/cmd/fleetctl/query.go
+++ b/cmd/fleetctl/query.go
@@ -9,69 +9,69 @@ import (
 	"time"
 
 	"github.com/briandowns/spinner"
-	"github.com/urfave/cli"
+	"github.com/urfave/cli/v2"
 )
 
-func queryCommand() cli.Command {
+func queryCommand() *cli.Command {
 	var (
 		flHosts, flLabels, flQuery, flQueryName string
 		flQuiet, flExit, flPretty               bool
 		flTimeout                               time.Duration
 	)
-	return cli.Command{
+	return &cli.Command{
 		Name:      "query",
 		Usage:     "Run a live query",
 		UsageText: `fleetctl query [options]`,
 		Flags: []cli.Flag{
-			cli.StringFlag{
+			&cli.StringFlag{
 				Name:        "hosts",
-				EnvVar:      "HOSTS",
+				EnvVars:     []string{"HOSTS"},
 				Value:       "",
 				Destination: &flHosts,
 				Usage:       "Comma separated hostnames to target",
 			},
-			cli.StringFlag{
+			&cli.StringFlag{
 				Name:        "labels",
-				EnvVar:      "LABELS",
+				EnvVars:     []string{"LABELS"},
 				Value:       "",
 				Destination: &flLabels,
 				Usage:       "Comma separated label names to target",
 			},
-			cli.BoolFlag{
+			&cli.BoolFlag{
 				Name:        "quiet",
-				EnvVar:      "QUIET",
+				EnvVars:     []string{"QUIET"},
 				Destination: &flQuiet,
 				Usage:       "Only print results (no status information)",
 			},
-			cli.BoolFlag{
+			&cli.BoolFlag{
 				Name:        "exit",
-				EnvVar:      "EXIT",
+				EnvVars:     []string{"EXIT"},
 				Destination: &flExit,
 				Usage:       "Exit when 100% of online hosts have results returned",
 			},
-			cli.StringFlag{
+			&cli.StringFlag{
 				Name:        "query",
-				EnvVar:      "QUERY",
+				EnvVars:     []string{"QUERY"},
 				Value:       "",
 				Destination: &flQuery,
 				Usage:       "Query to run",
 			},
-			cli.StringFlag{
+			&cli.StringFlag{
 				Name:        "query-name",
-				EnvVar:      "QUERYNAME",
+				EnvVars:     []string{"QUERYNAME"},
 				Value:       "",
 				Destination: &flQueryName,
 				Usage:       "Name of saved query to run",
 			},
-			cli.BoolFlag{
+			&cli.BoolFlag{
 				Name:        "pretty",
-				EnvVar:      "PRETTY",
+				EnvVars:     []string{"PRETTY"},
 				Destination: &flPretty,
 				Usage:       "Enable pretty-printing",
 			},
-			cli.DurationFlag{
+			&cli.DurationFlag{
 				Name:        "timeout",
-				EnvVar:      "TIMEOUT",
+				EnvVars:     []string{"TIMEOUT"},
 				Destination: &flTimeout,
 				Usage:       "How long to run query before exiting (10s, 1h, etc.)",
 			},
diff --git a/cmd/fleetctl/setup.go b/cmd/fleetctl/setup.go
index 209efad954..d69641731f 100644
--- a/cmd/fleetctl/setup.go
+++ b/cmd/fleetctl/setup.go
@@ -6,46 +6,46 @@ import (
 
 	"github.com/fleetdm/fleet/server/service"
 	"github.com/pkg/errors"
-	"github.com/urfave/cli"
+	"github.com/urfave/cli/v2"
 	"golang.org/x/crypto/ssh/terminal"
 )
 
-func setupCommand() cli.Command {
+func setupCommand() *cli.Command {
 	var (
 		flEmail    string
 		flUsername string
 		flPassword string
 		flOrgName  string
 	)
-	return cli.Command{
+	return &cli.Command{
 		Name:      "setup",
 		Usage:     "Set up a Fleet instance",
 		UsageText: `fleetctl setup [options]`,
 		Flags: []cli.Flag{
-			cli.StringFlag{
+			&cli.StringFlag{
 				Name:        "email",
-				EnvVar:      "EMAIL",
+				EnvVars:     []string{"EMAIL"},
 				Value:       "",
 				Destination: &flEmail,
 				Usage:       "Email of the admin user to create",
 			},
-			cli.StringFlag{
+			&cli.StringFlag{
 				Name:        "username",
-				EnvVar:      "USERNAME",
+				EnvVars:     []string{"USERNAME"},
 				Value:       "",
 				Destination: &flUsername,
 				Usage:       "Username of the admin user to create",
 			},
-			cli.StringFlag{
+			&cli.StringFlag{
 				Name:        "password",
-				EnvVar:      "PASSWORD",
+				EnvVars:     []string{"PASSWORD"},
 				Value:       "",
 				Destination: &flPassword,
 				Usage:       "Password for the admin user (recommended to use interactive entry)",
 			},
-			cli.StringFlag{
+			&cli.StringFlag{
 				Name:        "org-name",
-				EnvVar:      "ORG_NAME",
+				EnvVars:     []string{"ORG_NAME"},
 				Value:       "",
 				Destination: &flOrgName,
 				Usage:       "Name of the organization",
diff --git a/cmd/fleetctl/user.go b/cmd/fleetctl/user.go
index 98a986f3cb..8a0fc422da 100644
--- a/cmd/fleetctl/user.go
+++ b/cmd/fleetctl/user.go
@@ -7,7 +7,7 @@ import (
 
 	"github.com/fleetdm/fleet/server/kolide"
 	"github.com/pkg/errors"
-	"github.com/urfave/cli"
+	"github.com/urfave/cli/v2"
 	"golang.org/x/crypto/ssh/terminal"
 )
 
@@ -19,43 +19,43 @@ const (
 	ssoFlagName      = "sso"
 )
 
-func userCommand() cli.Command {
-	return cli.Command{
+func userCommand() *cli.Command {
+	return &cli.Command{
 		Name:  "user",
 		Usage: "Manage Fleet users",
-		Subcommands: []cli.Command{
+		Subcommands: []*cli.Command{
 			createUserCommand(),
 		},
 	}
 }
 
-func createUserCommand() cli.Command {
-	return cli.Command{
+func createUserCommand() *cli.Command {
+	return &cli.Command{
 		Name:  "create",
 		Usage: "Create a new user",
 		UsageText: `This command will create a new user in Fleet. By default, the user will authenticate with a password and will not have admin privileges.
 
    If a password is required and not provided by flag, the command will prompt for password input through stdin.`,
 		Flags: []cli.Flag{
-			cli.StringFlag{
+			&cli.StringFlag{
 				Name:     usernameFlagName,
 				Usage:    "Username for new user (required)",
 				Required: true,
 			},
-			cli.StringFlag{
+			&cli.StringFlag{
 				Name:     emailFlagName,
 				Usage:    "Email for new user (required)",
 				Required: true,
 			},
-			cli.StringFlag{
+			&cli.StringFlag{
 				Name:  passwordFlagName,
 				Usage: "Password for new user",
 			},
-			cli.BoolFlag{
+			&cli.BoolFlag{
 				Name:  adminFlagName,
 				Usage: "Grant admin privileges to created user (default false)",
 			},
-			cli.BoolFlag{
+			&cli.BoolFlag{
 				Name:  ssoFlagName,
 				Usage: "Enable user login via SSO (default false)",
 			},
diff --git a/go.mod b/go.mod
index d06517586e..0dc29cfbd3 100644
--- a/go.mod
+++ b/go.mod
@@ -48,6 +48,7 @@ require (
 	github.com/prometheus/client_golang v0.9.3-0.20190127221311-3c4408c8b829
 	github.com/russellhaering/gosaml2 v0.3.1
 	github.com/russellhaering/goxmldsig v1.1.0
+	github.com/russross/blackfriday/v2 v2.1.0 // indirect
 	github.com/spf13/afero v1.1.0 // indirect
 	github.com/spf13/cast v1.2.0
 	github.com/spf13/cobra v0.0.2
@@ -55,7 +56,7 @@ require (
 	github.com/spf13/pflag v1.0.1 // indirect
 	github.com/spf13/viper v1.0.2
 	github.com/stretchr/testify v1.6.1
-	github.com/urfave/cli v1.22.4
+	github.com/urfave/cli/v2 v2.3.0
 	github.com/ziutek/mymysql v1.5.4 // indirect
 	go.opencensus.io v0.20.2 // indirect
 	golang.org/x/crypto v0.0.0-20200622213623-75b288015ac9
@@ -66,5 +67,5 @@ require (
 	google.golang.org/grpc v1.19.0
 	gopkg.in/guregu/null.v3 v3.4.0
 	gopkg.in/natefinch/lumberjack.v2 v2.0.0-20170531160350-a96e63847dc3
-	gopkg.in/yaml.v2 v2.2.2
+	gopkg.in/yaml.v2 v2.2.3
 )
diff --git a/go.sum b/go.sum
index f2d3306812..e9425f3668 100644
--- a/go.sum
+++ b/go.sum
@@ -202,6 +202,8 @@ github.com/russellhaering/goxmldsig v1.1.0 h1:lK/zeJie2sqG52ZAlPNn1oBBqsIsEKypUU
 github.com/russellhaering/goxmldsig v1.1.0/go.mod h1:QK8GhXPB3+AfuCrfo0oRISa9NfzeCpWmxeGnqEpDF9o=
 github.com/russross/blackfriday/v2 v2.0.1 h1:lPqVAte+HuHNfhJ/0LC98ESWRz8afy9tM/0RK8m9o+Q=
 github.com/russross/blackfriday/v2 v2.0.1/go.mod h1:+Rmxgy9KzJVeS9/2gXHxylqXiyQDYRxCVz55jmeOWTM=
+github.com/russross/blackfriday/v2 v2.1.0 h1:JIOH55/0cWyOuilr9/qlrm0BSXldqnqwMsf35Ld67mk=
+github.com/russross/blackfriday/v2 v2.1.0/go.mod h1:+Rmxgy9KzJVeS9/2gXHxylqXiyQDYRxCVz55jmeOWTM=
 github.com/shurcooL/sanitized_anchor_name v1.0.0 h1:PdmoCO6wvbs+7yrJyMORt4/BmY5IYyJwS/kOiWx8mHo=
 github.com/shurcooL/sanitized_anchor_name v1.0.0/go.mod h1:1NzhyTcUVG4SuEtjjoZeVRXNmyL/1OwPU0+IJeTBvfc=
 github.com/sirupsen/logrus v1.2.0/go.mod h1:LxeOpSwHxABJmUn/MG1IvRgCAasNZTLOkJPxbbu5VWo=
@@ -226,8 +228,8 @@ github.com/stretchr/testify v1.5.1 h1:nOGnQDM7FYENwehXlg/kFVnos3rEvtKTjRvOWSzb6H
 github.com/stretchr/testify v1.5.1/go.mod h1:5W2xD1RspED5o8YsWQXVCued0rvSQ+mT+I5cxcmMvtA=
 github.com/stretchr/testify v1.6.1 h1:hDPOHmpOpP40lSULcqw7IrRb/u7w6RpDC9399XyoNd0=
 github.com/stretchr/testify v1.6.1/go.mod h1:6Fq8oRcR53rry900zMqJjRRixrwX3KX962/h/Wwjteg=
-github.com/urfave/cli v1.22.4 h1:u7tSpNPPswAFymm8IehJhy4uJMlUuU/GmqSkvJ1InXA=
-github.com/urfave/cli v1.22.4/go.mod h1:Gos4lmkARVdJ6EkW0WaNv/tZAAMe9V7XWyB60NtXRu0=
+github.com/urfave/cli/v2 v2.3.0 h1:qph92Y649prgesehzOrQjdWyxFOp/QVM+6imKHad91M=
+github.com/urfave/cli/v2 v2.3.0/go.mod h1:LJmUH05zAU44vOAcrfzZQKsZbVcdbOG8rtL3/XcUArI=
 github.com/zenazn/goji v0.9.0/go.mod h1:7S9M489iMyHBNxwZnk9/EHS098H4/F6TATF2mIxtB1Q=
 github.com/ziutek/mymysql v1.5.4 h1:GB0qdRGsTwQSBVYuVShFBKaXSnSnYYC2d9knnE1LHFs=
 github.com/ziutek/mymysql v1.5.4/go.mod h1:LMSpPZ6DbqWFxNCHW77HeMg9I646SAhApZ/wKdgO/C0=
@@ -320,6 +322,8 @@ gopkg.in/tomb.v1 v1.0.0-20141024135613-dd632973f1e7/go.mod h1:dt/ZhP58zS4L8KSrWD
 gopkg.in/yaml.v2 v2.2.1/go.mod h1:hI93XBmqTisBFMUTm0b8Fm+jr3Dg1NNxqwp+5A1VGuI=
 gopkg.in/yaml.v2 v2.2.2 h1:ZCJp+EgiOT7lHqUV2J862kp8Qj64Jo6az82+3Td9dZw=
 gopkg.in/yaml.v2 v2.2.2/go.mod h1:hI93XBmqTisBFMUTm0b8Fm+jr3Dg1NNxqwp+5A1VGuI=
+gopkg.in/yaml.v2 v2.2.3 h1:fvjTMHxHEw/mxHbtzPi3JCcKXQRAnQTBRo6YCJSVHKI=
+gopkg.in/yaml.v2 v2.2.3/go.mod h1:hI93XBmqTisBFMUTm0b8Fm+jr3Dg1NNxqwp+5A1VGuI=
 gopkg.in/yaml.v3 v3.0.0-20200313102051-9f266ea9e77c h1:dUUwHk2QECo/6vqA44rthZ8ie2QXMNeKRTHCNY2nXvo=
 gopkg.in/yaml.v3 v3.0.0-20200313102051-9f266ea9e77c/go.mod h1:K4uyk7z7BCEPqu6E+C64Yfv1cQ7kz7rIZviUmN+EgEM=
 honnef.co/go/tools v0.0.0-20180728063816-88497007e858/go.mod h1:rf3lG4BRIbNafJWhAfAdb/ePZxsR/4RtNHQocxwk9r4=