diff --git a/internal/cmd/base/base.go b/internal/cmd/base/base.go
index 86156ab916..e668743f31 100644
--- a/internal/cmd/base/base.go
+++ b/internal/cmd/base/base.go
@@ -69,13 +69,14 @@ const (
 	// maxLineLength is the maximum width of any line.
 	maxLineLength int = 78
 
-	envToken           = "BOUNDARY_TOKEN"
-	EnvTokenName       = "BOUNDARY_TOKEN_NAME"
-	EnvKeyringType     = "BOUNDARY_KEYRING_TYPE"
-	envRecoveryConfig  = "BOUNDARY_RECOVERY_CONFIG"
-	envSkipCacheDaemon = "BOUNDARY_SKIP_CACHE_DAEMON"
-	envSkipClientAgent = "BOUNDARY_SKIP_CLIENT_AGENT"
-	EnvClientAgentPort = "BOUNDARY_CLIENT_AGENT_LISTENING_PORT"
+	envToken                             = "BOUNDARY_TOKEN"
+	EnvTokenName                         = "BOUNDARY_TOKEN_NAME"
+	EnvKeyringType                       = "BOUNDARY_KEYRING_TYPE"
+	envRecoveryConfig                    = "BOUNDARY_RECOVERY_CONFIG"
+	envSkipCacheDaemon                   = "BOUNDARY_SKIP_CACHE_DAEMON"
+	envSkipClientAgent                   = "BOUNDARY_SKIP_CLIENT_AGENT"
+	EnvClientAgentPort                   = "BOUNDARY_CLIENT_AGENT_LISTENING_PORT"
+	EnvBoundaryClientAgentCliErrorOutput = "BOUNDARY_CLIENT_AGENT_CLI_ERROR_OUTPUT"
 
 	StoredTokenName = "HashiCorp Boundary Auth Token"
 )
@@ -107,14 +108,15 @@ type Command struct {
 	flagTLSServerName string
 	flagTLSInsecure   bool
 
-	flagFormat           string
-	FlagToken            string
-	FlagTokenName        string
-	FlagKeyringType      string
-	FlagRecoveryConfig   string
-	FlagOutputCurlString bool
-	FlagSkipCacheDaemon  bool
-	FlagSkipClientAgent  bool
+	flagFormat                    string
+	FlagToken                     string
+	FlagTokenName                 string
+	FlagKeyringType               string
+	FlagRecoveryConfig            string
+	FlagOutputCurlString          bool
+	FlagSkipCacheDaemon           bool
+	FlagSkipClientAgent           bool
+	FlagOutputClientAgentCliError bool
 
 	FlagClientAgentPort uint16
 
@@ -491,6 +493,14 @@ func (c *Command) FlagSet(bit FlagSetBit) *FlagSets {
 				Usage:   "Skips starting the caching daemon or sending the current used/retrieved token to the caching daemon.",
 			})
 
+			f.BoolVar(&BoolVar{
+				Name:    "output-client-agent-cli-error",
+				Target:  &c.FlagOutputClientAgentCliError,
+				Default: false,
+				EnvVar:  EnvBoundaryClientAgentCliErrorOutput,
+				Usage:   "Enables outputting CLI errors encountered for client-agent callbacks.",
+			})
+
 			f.BoolVar(&BoolVar{
 				Name:    "skip-client-agent",
 				Target:  &c.FlagSkipClientAgent,
diff --git a/internal/cmd/commands/clientagentcmd/addtoken.go b/internal/cmd/commands/clientagentcmd/addtoken.go
index 59ceb76ea7..5a60da9dcd 100644
--- a/internal/cmd/commands/clientagentcmd/addtoken.go
+++ b/internal/cmd/commands/clientagentcmd/addtoken.go
@@ -48,8 +48,8 @@ func addToken(ctx context.Context, apiClient *api.Client, port uint16) (*api.Res
 	client.RetryWaitMin = 100 * time.Millisecond
 	client.RetryWaitMax = 1500 * time.Millisecond
 
-	// Explicitly setting this to 1, since this runs after every command and we don't want any delays
-	client.RetryMax = 1
+	// Explicitly setting this to 0, since this runs after every command and we don't want any delays
+	client.RetryMax = 0
 
 	req, err := retryablehttp.NewRequestWithContext(ctx, "POST", clientAgentUrl(port, "v1/tokens"),
 		retryablehttp.ReaderFunc(func() (io.Reader, error) {
diff --git a/internal/cmd/commands/clientagentcmd/wrapper_register.go b/internal/cmd/commands/clientagentcmd/wrapper_register.go
index 4106b5f99a..3c4e7e2a47 100644
--- a/internal/cmd/commands/clientagentcmd/wrapper_register.go
+++ b/internal/cmd/commands/clientagentcmd/wrapper_register.go
@@ -5,24 +5,11 @@ package clientagentcmd
 
 import (
 	"context"
-	"os"
-	"strings"
 
 	"github.com/hashicorp/boundary/internal/cmd/base"
 	"github.com/hashicorp/boundary/internal/cmd/wrapper"
 )
 
-var allowErrorOutput = false
-
-const EnvBoundaryClientAgentCliErrorOutput = "BOUNDARY_CLIENT_AGENT_CLI_ERROR_OUTPUT"
-
-func init() {
-	errOutput := os.Getenv(EnvBoundaryClientAgentCliErrorOutput)
-	if strings.ToLower(errOutput) == "true" {
-		allowErrorOutput = true
-	}
-}
-
 func init() {
 	if err := wrapper.RegisterSuccessfulCommandCallback("client-agent", hook); err != nil {
 		panic(err)
@@ -34,7 +21,7 @@ func hook(ctx context.Context, baseCmd *base.Command, token string) {
 		return
 	}
 	client, err := baseCmd.Client()
-	if err != nil && allowErrorOutput {
+	if err != nil && baseCmd.FlagOutputClientAgentCliError {
 		baseCmd.PrintCliError(err)
 		return
 	}
@@ -42,10 +29,10 @@ func hook(ctx context.Context, baseCmd *base.Command, token string) {
 		client.SetToken(token)
 	}
 	_, apiErr, err := addToken(ctx, client, baseCmd.FlagClientAgentPort)
-	if err != nil && allowErrorOutput {
+	if err != nil && baseCmd.FlagOutputClientAgentCliError {
 		baseCmd.PrintCliError(err)
 	}
-	if apiErr != nil && allowErrorOutput {
+	if apiErr != nil && baseCmd.FlagOutputClientAgentCliError {
 		baseCmd.PrintApiError(apiErr, "sending token to client agent in the background")
 	}
 }