diff --git a/cli/cliflag/cliflag.go b/cli/cliflag/cliflag.go
index 7970fc2d64b58..4d93f8a77bc15 100644
--- a/cli/cliflag/cliflag.go
+++ b/cli/cliflag/cliflag.go
@@ -18,6 +18,8 @@ import (
 
 	"github.com/spf13/cobra"
 	"github.com/spf13/pflag"
+
+	"github.com/coder/coder/cli/cliui"
 )
 
 // IsSetBool returns the value of the boolean flag if it is set.
@@ -176,7 +178,7 @@ func fmtUsage(u string, env string) string {
 		if strings.HasSuffix(u, ".") {
 			dot = ""
 		}
-		u = fmt.Sprintf("%s%s\nConsumes $%s", u, dot, env)
+		u = fmt.Sprintf("%s%s\n"+cliui.Styles.Placeholder.Render("Consumes $%s"), u, dot, env)
 	}
 
 	return u
diff --git a/cli/cliui/cliui.go b/cli/cliui/cliui.go
index f1c0a13f2cd01..c9ff5c003ab97 100644
--- a/cli/cliui/cliui.go
+++ b/cli/cliui/cliui.go
@@ -48,7 +48,7 @@ var Styles = struct {
 	Field:         defaultStyles.Code.Copy().Foreground(lipgloss.AdaptiveColor{Light: "#000000", Dark: "#FFFFFF"}),
 	Keyword:       defaultStyles.Keyword,
 	Paragraph:     defaultStyles.Paragraph,
-	Placeholder:   lipgloss.NewStyle().Foreground(lipgloss.AdaptiveColor{Light: "#585858", Dark: "#005fff"}),
+	Placeholder:   lipgloss.NewStyle().Foreground(lipgloss.AdaptiveColor{Light: "#585858", Dark: "#4d46b3"}),
 	Prompt:        defaultStyles.Prompt.Foreground(lipgloss.AdaptiveColor{Light: "#9B9B9B", Dark: "#5C5C5C"}),
 	FocusedPrompt: defaultStyles.FocusedPrompt.Foreground(lipgloss.Color("#651fff")),
 	Fuchsia:       defaultStyles.SelectedMenuItem.Copy(),
diff --git a/cli/configssh.go b/cli/configssh.go
index 7ebb9dddf5d8b..0ff27ca29f16b 100644
--- a/cli/configssh.go
+++ b/cli/configssh.go
@@ -144,7 +144,7 @@ func configSSH() *cobra.Command {
 	cmd := &cobra.Command{
 		Annotations: workspaceCommand,
 		Use:         "config-ssh",
-		Short:       "Populate your SSH config with Host entries for all of your workspaces",
+		Short:       "Add an SSH Host entry for your workspaces \"ssh coder.workspace\"",
 		Example: formatExamples(
 			example{
 				Description: "You can use -o (or --ssh-option) so set SSH options to be used for all your workspaces",
diff --git a/cli/create.go b/cli/create.go
index 86e8ff016ce4e..55281741fc6bc 100644
--- a/cli/create.go
+++ b/cli/create.go
@@ -25,7 +25,7 @@ func create() *cobra.Command {
 	cmd := &cobra.Command{
 		Annotations: workspaceCommand,
 		Use:         "create [name]",
-		Short:       "Create a workspace from a template",
+		Short:       "Create a workspace",
 		RunE: func(cmd *cobra.Command, args []string) error {
 			client, err := CreateClient(cmd)
 			if err != nil {
diff --git a/cli/dotfiles.go b/cli/dotfiles.go
index 11c24af1710fc..0d9248250ceca 100644
--- a/cli/dotfiles.go
+++ b/cli/dotfiles.go
@@ -22,7 +22,7 @@ func dotfiles() *cobra.Command {
 	cmd := &cobra.Command{
 		Use:   "dotfiles [git_repo_url]",
 		Args:  cobra.ExactArgs(1),
-		Short: "Check out and install a dotfiles repository.",
+		Short: "Checkout and install a dotfiles repository from a Git URL",
 		Example: formatExamples(
 			example{
 				Description: "Check out and install a dotfiles repository without prompts",
diff --git a/cli/features.go b/cli/features.go
index f430534330816..8b5d8ba30d680 100644
--- a/cli/features.go
+++ b/cli/features.go
@@ -15,7 +15,7 @@ import (
 
 func features() *cobra.Command {
 	cmd := &cobra.Command{
-		Short:   "List features",
+		Short:   "List Enterprise features",
 		Use:     "features",
 		Aliases: []string{"feature"},
 	}
diff --git a/cli/list.go b/cli/list.go
index fe664bd4f9052..f1dfe098e96c1 100644
--- a/cli/list.go
+++ b/cli/list.go
@@ -66,7 +66,7 @@ func list() *cobra.Command {
 	cmd := &cobra.Command{
 		Annotations: workspaceCommand,
 		Use:         "list",
-		Short:       "List all workspaces",
+		Short:       "List workspaces",
 		Aliases:     []string{"ls"},
 		Args:        cobra.ExactArgs(0),
 		RunE: func(cmd *cobra.Command, args []string) error {
diff --git a/cli/login.go b/cli/login.go
index dfc35fcc9ecc8..776c0cdb21a95 100644
--- a/cli/login.go
+++ b/cli/login.go
@@ -45,7 +45,7 @@ func login() *cobra.Command {
 	)
 	cmd := &cobra.Command{
 		Use:   "login <url>",
-		Short: "Authenticate with a Coder deployment",
+		Short: "Authenticate with Coder deployment",
 		Args:  cobra.ExactArgs(1),
 		RunE: func(cmd *cobra.Command, args []string) error {
 			rawURL := args[0]
diff --git a/cli/logout.go b/cli/logout.go
index 3ad84e7b61163..e0d01b306d0e5 100644
--- a/cli/logout.go
+++ b/cli/logout.go
@@ -14,7 +14,7 @@ import (
 func logout() *cobra.Command {
 	cmd := &cobra.Command{
 		Use:   "logout",
-		Short: "Remove the local authenticated session",
+		Short: "Unauthenticate your local session",
 		RunE: func(cmd *cobra.Command, args []string) error {
 			client, err := CreateClient(cmd)
 			if err != nil {
diff --git a/cli/portforward.go b/cli/portforward.go
index e420149affec4..bdcceab723daa 100644
--- a/cli/portforward.go
+++ b/cli/portforward.go
@@ -32,7 +32,7 @@ func portForward() *cobra.Command {
 	)
 	cmd := &cobra.Command{
 		Use:     "port-forward <workspace>",
-		Short:   "Forward one or more ports from the local machine to the remote workspace",
+		Short:   "Forward ports from machine to a workspace",
 		Aliases: []string{"tunnel"},
 		Args:    cobra.ExactArgs(1),
 		Example: formatExamples(
diff --git a/cli/publickey.go b/cli/publickey.go
index 5b603516ba7fa..6926ecf3227b8 100644
--- a/cli/publickey.go
+++ b/cli/publickey.go
@@ -18,7 +18,7 @@ func publickey() *cobra.Command {
 	cmd := &cobra.Command{
 		Use:     "publickey",
 		Aliases: []string{"pubkey"},
-		Short:   "Output your public key for Git operations",
+		Short:   "Output your Coder public key used for Git operations",
 		RunE: func(cmd *cobra.Command, args []string) error {
 			client, err := CreateClient(cmd)
 			if err != nil {
diff --git a/cli/resetpassword.go b/cli/resetpassword.go
index e33483243fa0b..7c0475ad01e4c 100644
--- a/cli/resetpassword.go
+++ b/cli/resetpassword.go
@@ -20,7 +20,7 @@ func resetPassword() *cobra.Command {
 
 	root := &cobra.Command{
 		Use:   "reset-password <username>",
-		Short: "Reset a user's password by directly updating the database",
+		Short: "Directly connect to the database to reset a user's password",
 		Args:  cobra.ExactArgs(1),
 		RunE: func(cmd *cobra.Command, args []string) error {
 			username := args[0]
diff --git a/cli/root.go b/cli/root.go
index 0af53d2f7f687..c3e8c6d244384 100644
--- a/cli/root.go
+++ b/cli/root.go
@@ -167,21 +167,21 @@ func Root(subcommands []*cobra.Command) *cobra.Command {
 
 	cmd.SetUsageTemplate(usageTemplate())
 
-	cmd.PersistentFlags().String(varURL, "", "Specify the URL to your deployment.")
+	cmd.PersistentFlags().String(varURL, "", "URL to a deployment.")
 	cliflag.Bool(cmd.PersistentFlags(), varNoVersionCheck, "", envNoVersionCheck, false, "Suppress warning when client and server versions do not match.")
 	cliflag.Bool(cmd.PersistentFlags(), varNoFeatureWarning, "", envNoFeatureWarning, false, "Suppress warnings about unlicensed features.")
 	cliflag.String(cmd.PersistentFlags(), varToken, "", envSessionToken, "", fmt.Sprintf("Specify an authentication token. For security reasons setting %s is preferred.", envSessionToken))
-	cliflag.String(cmd.PersistentFlags(), varAgentToken, "", "CODER_AGENT_TOKEN", "", "Specify an agent authentication token.")
+	cliflag.String(cmd.PersistentFlags(), varAgentToken, "", "CODER_AGENT_TOKEN", "", "An agent authentication token.")
 	_ = cmd.PersistentFlags().MarkHidden(varAgentToken)
-	cliflag.String(cmd.PersistentFlags(), varAgentURL, "", "CODER_AGENT_URL", "", "Specify the URL for an agent to access your deployment.")
+	cliflag.String(cmd.PersistentFlags(), varAgentURL, "", "CODER_AGENT_URL", "", "URL for an agent to access your deployment.")
 	_ = cmd.PersistentFlags().MarkHidden(varAgentURL)
-	cliflag.String(cmd.PersistentFlags(), varGlobalConfig, "", "CODER_CONFIG_DIR", configdir.LocalConfig("coderv2"), "Specify the path to the global `coder` config directory.")
+	cliflag.String(cmd.PersistentFlags(), varGlobalConfig, "", "CODER_CONFIG_DIR", configdir.LocalConfig("coderv2"), "Path to the global `coder` config directory.")
 	cliflag.StringArray(cmd.PersistentFlags(), varHeader, "", "CODER_HEADER", []string{}, "HTTP headers added to all requests. Provide as \"Key=Value\"")
 	cmd.PersistentFlags().Bool(varForceTty, false, "Force the `coder` command to run as if connected to a TTY.")
 	_ = cmd.PersistentFlags().MarkHidden(varForceTty)
 	cmd.PersistentFlags().Bool(varNoOpen, false, "Block automatically opening URLs in the browser.")
 	_ = cmd.PersistentFlags().MarkHidden(varNoOpen)
-	cliflag.Bool(cmd.PersistentFlags(), varVerbose, "v", "CODER_VERBOSE", false, "Enable verbose output")
+	cliflag.Bool(cmd.PersistentFlags(), varVerbose, "v", "CODER_VERBOSE", false, "Enable verbose output.")
 
 	return cmd
 }
diff --git a/cli/schedule.go b/cli/schedule.go
index 73ddf141c151b..1e6b5b274bb6c 100644
--- a/cli/schedule.go
+++ b/cli/schedule.go
@@ -57,7 +57,7 @@ func schedules() *cobra.Command {
 	scheduleCmd := &cobra.Command{
 		Annotations: workspaceCommand,
 		Use:         "schedule { show | start | stop | override } <workspace>",
-		Short:       "Modify scheduled stop and start times for your workspace",
+		Short:       "Schedule automated start and stop times for workspaces",
 	}
 
 	scheduleCmd.AddCommand(
diff --git a/cli/server.go b/cli/server.go
index 3ece155bd3c3d..bade52d7403f4 100644
--- a/cli/server.go
+++ b/cli/server.go
@@ -755,95 +755,119 @@ func Server(newAPI func(*coderd.Options) *coderd.API) *cobra.Command {
 		},
 	})
 
-	cliflag.DurationVarP(root.Flags(), &autobuildPollInterval, "autobuild-poll-interval", "", "CODER_AUTOBUILD_POLL_INTERVAL", time.Minute, "Specifies the interval at which to poll for and execute automated workspace build operations.")
-	cliflag.StringVarP(root.Flags(), &accessURL, "access-url", "", "CODER_ACCESS_URL", "", "Specifies the external URL to access Coder.")
-	cliflag.StringVarP(root.Flags(), &address, "address", "a", "CODER_ADDRESS", "127.0.0.1:3000", "The address to serve the API and dashboard.")
+	cliflag.DurationVarP(root.Flags(), &autobuildPollInterval, "autobuild-poll-interval", "", "CODER_AUTOBUILD_POLL_INTERVAL", time.Minute,
+		"Interval to poll for scheduled workspace builds.")
+	_ = root.Flags().MarkHidden("autobuild-poll-interval")
+	cliflag.StringVarP(root.Flags(), &accessURL, "access-url", "", "CODER_ACCESS_URL", "",
+		"External URL to access your deployment. This must be accessible by all provisioned workspaces.")
+	cliflag.StringVarP(root.Flags(), &address, "address", "a", "CODER_ADDRESS", "127.0.0.1:3000",
+		"Bind address of the server.")
 	cliflag.StringVarP(root.Flags(), &derpConfigURL, "derp-config-url", "", "CODER_DERP_CONFIG_URL", "",
-		"Specifies a URL to periodically fetch a DERP map. See: https://tailscale.com/kb/1118/custom-derp-servers/")
+		"URL to fetch a DERP mapping on startup. See: https://tailscale.com/kb/1118/custom-derp-servers/")
 	cliflag.StringVarP(root.Flags(), &derpConfigPath, "derp-config-path", "", "CODER_DERP_CONFIG_PATH", "",
-		"Specifies a path to read a DERP map from. See: https://tailscale.com/kb/1118/custom-derp-servers/")
-	cliflag.BoolVarP(root.Flags(), &derpServerEnabled, "derp-server-enable", "", "CODER_DERP_SERVER_ENABLE", true, "Specifies whether to enable or disable the embedded DERP server.")
-	cliflag.IntVarP(root.Flags(), &derpServerRegionID, "derp-server-region-id", "", "CODER_DERP_SERVER_REGION_ID", 999, "Specifies the region ID to use for the embedded DERP server.")
-	cliflag.StringVarP(root.Flags(), &derpServerRegionCode, "derp-server-region-code", "", "CODER_DERP_SERVER_REGION_CODE", "coder", "Specifies the region code that is displayed in the Coder UI for the embedded DERP server.")
-	cliflag.StringVarP(root.Flags(), &derpServerRegionName, "derp-server-region-name", "", "CODER_DERP_SERVER_REGION_NAME", "Coder Embedded Relay", "Specifies the region name that is displayed in the Coder UI for the embedded DERP server.")
+		"Path to read a DERP mapping from. See: https://tailscale.com/kb/1118/custom-derp-servers/")
+	cliflag.BoolVarP(root.Flags(), &derpServerEnabled, "derp-server-enable", "", "CODER_DERP_SERVER_ENABLE", true,
+		"Whether to enable or disable the embedded DERP relay server.")
+	cliflag.IntVarP(root.Flags(), &derpServerRegionID, "derp-server-region-id", "", "CODER_DERP_SERVER_REGION_ID", 999,
+		"Region ID to use for the embedded DERP server.")
+	cliflag.StringVarP(root.Flags(), &derpServerRegionCode, "derp-server-region-code", "", "CODER_DERP_SERVER_REGION_CODE", "coder",
+		"Region code that for the embedded DERP server.")
+	cliflag.StringVarP(root.Flags(), &derpServerRegionName, "derp-server-region-name", "", "CODER_DERP_SERVER_REGION_NAME", "Coder Embedded Relay",
+		"Region name that for the embedded DERP server.")
 	cliflag.StringArrayVarP(root.Flags(), &derpServerSTUNAddrs, "derp-server-stun-addresses", "", "CODER_DERP_SERVER_STUN_ADDRESSES", []string{
 		"stun.l.google.com:19302",
-	}, "Specify addresses for STUN servers to establish P2P connections. Set empty to disable P2P connections entirely.")
-	cliflag.BoolVarP(root.Flags(), &promEnabled, "prometheus-enable", "", "CODER_PROMETHEUS_ENABLE", false, "Enable serving prometheus metrics on the addressdefined by --prometheus-address.")
-	cliflag.StringVarP(root.Flags(), &promAddress, "prometheus-address", "", "CODER_PROMETHEUS_ADDRESS", "127.0.0.1:2112", "The address to serve prometheus metrics.")
-	cliflag.BoolVarP(root.Flags(), &pprofEnabled, "pprof-enable", "", "CODER_PPROF_ENABLE", false, "Enable serving pprof metrics on the address defined by --pprof-address.")
-	cliflag.StringVarP(root.Flags(), &pprofAddress, "pprof-address", "", "CODER_PPROF_ADDRESS", "127.0.0.1:6060", "The address to serve pprof.")
+	}, "Addresses for STUN servers to establish P2P connections. Set empty to disable P2P connections.")
+	cliflag.BoolVarP(root.Flags(), &promEnabled, "prometheus-enable", "", "CODER_PROMETHEUS_ENABLE", false,
+		"Serve prometheus metrics on the address defined by `prometheus-address`.")
+	cliflag.StringVarP(root.Flags(), &promAddress, "prometheus-address", "", "CODER_PROMETHEUS_ADDRESS", "127.0.0.1:2112",
+		"The bind address to serve prometheus metrics.")
+	cliflag.BoolVarP(root.Flags(), &pprofEnabled, "pprof-enable", "", "CODER_PPROF_ENABLE", false,
+		"Serve pprof metrics on the address defined by `pprof-address`.")
+	cliflag.StringVarP(root.Flags(), &pprofAddress, "pprof-address", "", "CODER_PPROF_ADDRESS", "127.0.0.1:6060",
+		"The bind address to serve pprof.")
 	defaultCacheDir := filepath.Join(os.TempDir(), "coder-cache")
 	if dir := os.Getenv("CACHE_DIRECTORY"); dir != "" {
 		// For compatibility with systemd.
 		defaultCacheDir = dir
 	}
-	cliflag.StringVarP(root.Flags(), &cacheDir, "cache-dir", "", "CODER_CACHE_DIRECTORY", defaultCacheDir, "Specifies a directory to cache binaries for provision operations. If unspecified and $CACHE_DIRECTORY is set, it will be used for compatibility with systemd.")
+	cliflag.StringVarP(root.Flags(), &cacheDir, "cache-dir", "", "CODER_CACHE_DIRECTORY", defaultCacheDir,
+		"The directory to cache temporary files. If unspecified and $CACHE_DIRECTORY is set, it will be used for compatibility with systemd.")
 	cliflag.BoolVarP(root.Flags(), &inMemoryDatabase, "in-memory", "", "CODER_INMEMORY", false,
-		"Specifies whether data will be stored in an in-memory database.")
+		"Controls whether data will be stored in an in-memory database.")
 	_ = root.Flags().MarkHidden("in-memory")
-	cliflag.StringVarP(root.Flags(), &postgresURL, "postgres-url", "", "CODER_PG_CONNECTION_URL", "", "The URL of a PostgreSQL database to connect to. If empty, PostgreSQL binaries will be downloaded from Maven (https://repo1.maven.org/maven2) and store all data in the config root. Access the built-in database with \"coder server postgres-builtin-url\"")
-	cliflag.Uint8VarP(root.Flags(), &provisionerDaemonCount, "provisioner-daemons", "", "CODER_PROVISIONER_DAEMONS", 3, "The amount of provisioner daemons to create on start.")
+	cliflag.StringVarP(root.Flags(), &postgresURL, "postgres-url", "", "CODER_PG_CONNECTION_URL", "",
+		"URL of a PostgreSQL database. If empty, PostgreSQL binaries will be downloaded from Maven (https://repo1.maven.org/maven2) and store all data in the config root. Access the built-in database with \"coder server postgres-builtin-url\"")
+	cliflag.Uint8VarP(root.Flags(), &provisionerDaemonCount, "provisioner-daemons", "", "CODER_PROVISIONER_DAEMONS", 3,
+		"Number of provisioner daemons to create on start. If builds are stuck in queued state for a long time, consider increasing this.")
 	cliflag.StringVarP(root.Flags(), &oauth2GithubClientID, "oauth2-github-client-id", "", "CODER_OAUTH2_GITHUB_CLIENT_ID", "",
-		"Specifies a client ID to use for oauth2 with GitHub.")
+		"Client ID for Login with GitHub.")
 	cliflag.StringVarP(root.Flags(), &oauth2GithubClientSecret, "oauth2-github-client-secret", "", "CODER_OAUTH2_GITHUB_CLIENT_SECRET", "",
-		"Specifies a client secret to use for oauth2 with GitHub.")
+		"Client secret for Login with GitHub.")
 	cliflag.StringArrayVarP(root.Flags(), &oauth2GithubAllowedOrganizations, "oauth2-github-allowed-orgs", "", "CODER_OAUTH2_GITHUB_ALLOWED_ORGS", nil,
-		"Specifies organizations the user must be a member of to authenticate with GitHub.")
+		"Organizations the user must be a member of to Login with GitHub.")
 	cliflag.StringArrayVarP(root.Flags(), &oauth2GithubAllowedTeams, "oauth2-github-allowed-teams", "", "CODER_OAUTH2_GITHUB_ALLOWED_TEAMS", nil,
-		"Specifies teams inside organizations the user must be a member of to authenticate with GitHub. Formatted as: <organization-name>/<team-slug>.")
+		"Teams inside organizations the user must be a member of to Login with GitHub. Structured as: <organization-name>/<team-slug>.")
 	cliflag.BoolVarP(root.Flags(), &oauth2GithubAllowSignups, "oauth2-github-allow-signups", "", "CODER_OAUTH2_GITHUB_ALLOW_SIGNUPS", false,
-		"Specifies whether new users can sign up with GitHub.")
+		"Whether new users can sign up with GitHub.")
 	cliflag.StringVarP(root.Flags(), &oauth2GithubEnterpriseBaseURL, "oauth2-github-enterprise-base-url", "", "CODER_OAUTH2_GITHUB_ENTERPRISE_BASE_URL", "",
-		"Specifies the base URL of a GitHub Enterprise instance to use for oauth2.")
+		"Base URL of a GitHub Enterprise deployment to use for Login with GitHub.")
 	cliflag.BoolVarP(root.Flags(), &oidcAllowSignups, "oidc-allow-signups", "", "CODER_OIDC_ALLOW_SIGNUPS", true,
-		"Specifies whether new users can sign up with OIDC.")
+		"Whether new users can sign up with OIDC.")
 	cliflag.StringVarP(root.Flags(), &oidcClientID, "oidc-client-id", "", "CODER_OIDC_CLIENT_ID", "",
-		"Specifies a client ID to use for OIDC.")
+		"Client ID to use for Login with OIDC.")
 	cliflag.StringVarP(root.Flags(), &oidcClientSecret, "oidc-client-secret", "", "CODER_OIDC_CLIENT_SECRET", "",
-		"Specifies a client secret to use for OIDC.")
+		"Client secret to use for Login with OIDC.")
 	cliflag.StringVarP(root.Flags(), &oidcEmailDomain, "oidc-email-domain", "", "CODER_OIDC_EMAIL_DOMAIN", "",
-		"Specifies an email domain that clients authenticating with OIDC must match.")
+		"Email domain that clients logging in with OIDC must match.")
 	cliflag.StringVarP(root.Flags(), &oidcIssuerURL, "oidc-issuer-url", "", "CODER_OIDC_ISSUER_URL", "",
-		"Specifies an issuer URL to use for OIDC.")
+		"Issuer URL to use for Login with OIDC.")
 	cliflag.StringArrayVarP(root.Flags(), &oidcScopes, "oidc-scopes", "", "CODER_OIDC_SCOPES", []string{oidc.ScopeOpenID, "profile", "email"},
-		"Specifies scopes to grant when authenticating with OIDC.")
+		"Scopes to grant when authenticating with OIDC.")
 	cliflag.BoolVarP(root.Flags(), &tailscaleEnable, "tailscale", "", "CODER_TAILSCALE", true,
 		"Specifies whether Tailscale networking is used for web applications and terminals.")
 	_ = root.Flags().MarkHidden("tailscale")
 	enableTelemetryByDefault := !isTest()
-	cliflag.BoolVarP(root.Flags(), &telemetryEnable, "telemetry", "", "CODER_TELEMETRY", enableTelemetryByDefault, "Specifies whether telemetry is enabled or not. Coder collects anonymized usage data to help improve our product.")
-	cliflag.StringVarP(root.Flags(), &telemetryURL, "telemetry-url", "", "CODER_TELEMETRY_URL", "https://telemetry.coder.com", "Specifies a URL to send telemetry to.")
+	cliflag.BoolVarP(root.Flags(), &telemetryEnable, "telemetry", "", "CODER_TELEMETRY", enableTelemetryByDefault,
+		"Whether telemetry is enabled or not. Coder collects anonymized usage data to help improve our product.")
+	cliflag.StringVarP(root.Flags(), &telemetryURL, "telemetry-url", "", "CODER_TELEMETRY_URL", "https://telemetry.coder.com",
+		"URL to send telemetry.")
 	_ = root.Flags().MarkHidden("telemetry-url")
-	cliflag.BoolVarP(root.Flags(), &tlsEnable, "tls-enable", "", "CODER_TLS_ENABLE", false, "Specifies if TLS will be enabled")
+	cliflag.BoolVarP(root.Flags(), &tlsEnable, "tls-enable", "", "CODER_TLS_ENABLE", false,
+		"Whether TLS will be enabled.")
 	cliflag.StringVarP(root.Flags(), &tlsCertFile, "tls-cert-file", "", "CODER_TLS_CERT_FILE", "",
-		"Specifies the path to the certificate for TLS. It requires a PEM-encoded file. "+
+		"Path to the certificate for TLS. It requires a PEM-encoded file. "+
 			"To configure the listener to use a CA certificate, concatenate the primary certificate "+
-			"and the CA certificate together. The primary certificate should appear first in the combined file")
+			"and the CA certificate together. The primary certificate should appear first in the combined file.")
 	cliflag.StringVarP(root.Flags(), &tlsClientCAFile, "tls-client-ca-file", "", "CODER_TLS_CLIENT_CA_FILE", "",
 		"PEM-encoded Certificate Authority file used for checking the authenticity of client")
 	cliflag.StringVarP(root.Flags(), &tlsClientAuth, "tls-client-auth", "", "CODER_TLS_CLIENT_AUTH", "request",
-		`Specifies the policy the server will follow for TLS Client Authentication. `+
+		`Policy the server will follow for TLS Client Authentication. `+
 			`Accepted values are "none", "request", "require-any", "verify-if-given", or "require-and-verify"`)
 	cliflag.StringVarP(root.Flags(), &tlsKeyFile, "tls-key-file", "", "CODER_TLS_KEY_FILE", "",
-		"Specifies the path to the private key for the certificate. It requires a PEM-encoded file")
+		"Path to the private key for the certificate. It requires a PEM-encoded file")
 	cliflag.StringVarP(root.Flags(), &tlsMinVersion, "tls-min-version", "", "CODER_TLS_MIN_VERSION", "tls12",
-		`Specifies the minimum supported version of TLS. Accepted values are "tls10", "tls11", "tls12" or "tls13"`)
+		`Minimum supported version of TLS. Accepted values are "tls10", "tls11", "tls12" or "tls13"`)
 	cliflag.BoolVarP(root.Flags(), &tunnel, "tunnel", "", "CODER_TUNNEL", false,
 		"Workspaces must be able to reach the `access-url`. This overrides your access URL with a public access URL that tunnels your Coder deployment.")
 	cliflag.StringArrayVarP(root.Flags(), &stunServers, "stun-server", "", "CODER_STUN_SERVERS", []string{
 		"stun:stun.l.google.com:19302",
-	}, "Specify URLs for STUN servers to enable P2P connections.")
-	cliflag.BoolVarP(root.Flags(), &traceEnable, "trace", "", "CODER_TRACE", false, "Specifies if application tracing data is collected")
+	}, "URLs for STUN servers to enable P2P connections.")
+	cliflag.BoolVarP(root.Flags(), &traceEnable, "trace", "", "CODER_TRACE", false,
+		"Whether application tracing data is collected.")
 	cliflag.StringVarP(root.Flags(), &turnRelayAddress, "turn-relay-address", "", "CODER_TURN_RELAY_ADDRESS", "127.0.0.1",
-		"Specifies the address to bind TURN connections.")
-	cliflag.BoolVarP(root.Flags(), &secureAuthCookie, "secure-auth-cookie", "", "CODER_SECURE_AUTH_COOKIE", false, "Specifies if the 'Secure' property is set on browser session cookies")
-	cliflag.StringVarP(root.Flags(), &sshKeygenAlgorithmRaw, "ssh-keygen-algorithm", "", "CODER_SSH_KEYGEN_ALGORITHM", "ed25519", "Specifies the algorithm to use for generating ssh keys. "+
-		`Accepted values are "ed25519", "ecdsa", or "rsa4096"`)
-	cliflag.StringArrayVarP(root.Flags(), &autoImportTemplates, "auto-import-template", "", "CODER_TEMPLATE_AUTOIMPORT", []string{}, "Which templates to auto-import. Available auto-importable templates are: kubernetes")
-	cliflag.BoolVarP(root.Flags(), &spooky, "spooky", "", "", false, "Specifies spookiness level")
+		"The address to bind TURN connections.")
+	cliflag.BoolVarP(root.Flags(), &secureAuthCookie, "secure-auth-cookie", "", "CODER_SECURE_AUTH_COOKIE", false,
+		"Controls if the 'Secure' property is set on browser session cookies")
+	cliflag.StringVarP(root.Flags(), &sshKeygenAlgorithmRaw, "ssh-keygen-algorithm", "", "CODER_SSH_KEYGEN_ALGORITHM", "ed25519",
+		"The algorithm to use for generating ssh keys. "+
+			`Accepted values are "ed25519", "ecdsa", or "rsa4096"`)
+	cliflag.StringArrayVarP(root.Flags(), &autoImportTemplates, "auto-import-template", "", "CODER_TEMPLATE_AUTOIMPORT", []string{},
+		"Templates to auto-import. Available auto-importable templates are: kubernetes")
+	_ = root.Flags().MarkHidden("auto-import-template")
+	cliflag.BoolVarP(root.Flags(), &spooky, "spooky", "", "", false, "Specifies spookiness level...")
 	_ = root.Flags().MarkHidden("spooky")
-	cliflag.BoolVarP(root.Flags(), &verbose, "verbose", "v", "CODER_VERBOSE", false, "Enables verbose logging.")
+	cliflag.BoolVarP(root.Flags(), &verbose, "verbose", "v", "CODER_VERBOSE", false,
+		"Enables verbose logging.")
 
 	// These metrics flags are for manually testing the metric system.
 	// The defaults should be acceptable for any Coder deployment of any
@@ -851,7 +875,7 @@ func Server(newAPI func(*coderd.Options) *coderd.API) *cobra.Command {
 	cliflag.DurationVarP(root.Flags(), &metricsCacheRefreshInterval, "metrics-cache-refresh-interval", "", "CODER_METRICS_CACHE_REFRESH_INTERVAL", time.Hour, "How frequently metrics are refreshed")
 	_ = root.Flags().MarkHidden("metrics-cache-refresh-interval")
 	cliflag.DurationVarP(root.Flags(), &agentStatRefreshInterval, "agent-stats-refresh-interval", "", "CODER_AGENT_STATS_REFRESH_INTERVAL", time.Minute*10, "How frequently agent stats are recorded")
-	_ = root.Flags().MarkHidden("agent-stats-report-interval")
+	_ = root.Flags().MarkHidden("agent-stats-refresh-interval")
 
 	return root
 }
diff --git a/cli/show.go b/cli/show.go
index 069b464645edb..0035fabb7cc0a 100644
--- a/cli/show.go
+++ b/cli/show.go
@@ -11,7 +11,7 @@ func show() *cobra.Command {
 	return &cobra.Command{
 		Annotations: workspaceCommand,
 		Use:         "show <workspace>",
-		Short:       "Show details of a workspace's resources and agents",
+		Short:       "Display details of a workspace's resources and agents",
 		Args:        cobra.ExactArgs(1),
 		RunE: func(cmd *cobra.Command, args []string) error {
 			client, err := CreateClient(cmd)
diff --git a/cli/speedtest.go b/cli/speedtest.go
index ab1586815b621..f1e177d4eb22d 100644
--- a/cli/speedtest.go
+++ b/cli/speedtest.go
@@ -28,7 +28,7 @@ func speedtest() *cobra.Command {
 		Annotations: workspaceCommand,
 		Use:         "speedtest <workspace>",
 		Args:        cobra.ExactArgs(1),
-		Short:       "Run a speed test from your machine to the workspace.",
+		Short:       "Run upload and download tests from your machine to a workspace",
 		RunE: func(cmd *cobra.Command, args []string) error {
 			ctx, cancel := context.WithCancel(cmd.Context())
 			defer cancel()
diff --git a/cli/ssh.go b/cli/ssh.go
index 21ac08ed772f0..96b243bab828a 100644
--- a/cli/ssh.go
+++ b/cli/ssh.go
@@ -48,7 +48,7 @@ func ssh() *cobra.Command {
 	cmd := &cobra.Command{
 		Annotations: workspaceCommand,
 		Use:         "ssh <workspace>",
-		Short:       "SSH into a workspace",
+		Short:       "Start a shell into a workspace",
 		Args:        cobra.ArbitraryArgs,
 		RunE: func(cmd *cobra.Command, args []string) error {
 			ctx, cancel := context.WithCancel(cmd.Context())
diff --git a/cli/start.go b/cli/start.go
index 9ceeed2c2b998..7abcd036a4456 100644
--- a/cli/start.go
+++ b/cli/start.go
@@ -14,7 +14,7 @@ func start() *cobra.Command {
 	cmd := &cobra.Command{
 		Annotations: workspaceCommand,
 		Use:         "start <workspace>",
-		Short:       "Build a workspace with the start state",
+		Short:       "Start a workspace",
 		Args:        cobra.ExactArgs(1),
 		RunE: func(cmd *cobra.Command, args []string) error {
 			client, err := CreateClient(cmd)
diff --git a/cli/stop.go b/cli/stop.go
index c2bfa76e4df02..1b99c0251ccee 100644
--- a/cli/stop.go
+++ b/cli/stop.go
@@ -14,7 +14,7 @@ func stop() *cobra.Command {
 	cmd := &cobra.Command{
 		Annotations: workspaceCommand,
 		Use:         "stop <workspace>",
-		Short:       "Build a workspace with the stop state",
+		Short:       "Stop a workspace",
 		Args:        cobra.ExactArgs(1),
 		RunE: func(cmd *cobra.Command, args []string) error {
 			_, err := cliui.Prompt(cmd, cliui.PromptOptions{
diff --git a/cli/templates.go b/cli/templates.go
index cb4a028f2605c..5e18d4d188e27 100644
--- a/cli/templates.go
+++ b/cli/templates.go
@@ -13,7 +13,8 @@ import (
 func templates() *cobra.Command {
 	cmd := &cobra.Command{
 		Use:     "templates",
-		Short:   "Create, manage, and deploy templates",
+		Short:   "Manage templates",
+		Long:    "Templates are written in standard Terraform and describe the infrastructure for workspaces",
 		Aliases: []string{"template"},
 		Example: formatExamples(
 			example{
diff --git a/cli/update.go b/cli/update.go
index ed3a900cc1917..f80aaadfca65c 100644
--- a/cli/update.go
+++ b/cli/update.go
@@ -20,7 +20,7 @@ func update() *cobra.Command {
 		Annotations: workspaceCommand,
 		Use:         "update <workspace>",
 		Args:        cobra.ExactArgs(1),
-		Short:       "Update a workspace to the latest template version",
+		Short:       "Update a workspace",
 		RunE: func(cmd *cobra.Command, args []string) error {
 			client, err := CreateClient(cmd)
 			if err != nil {
diff --git a/cli/users.go b/cli/users.go
index daadc2007fa74..3c8368e4d1b10 100644
--- a/cli/users.go
+++ b/cli/users.go
@@ -8,7 +8,7 @@ import (
 
 func users() *cobra.Command {
 	cmd := &cobra.Command{
-		Short:   "Create, remove, and list users",
+		Short:   "Manage users",
 		Use:     "users",
 		Aliases: []string{"user"},
 	}