diff --git a/internal/cmd/commands/accountscmd/funcs.go b/internal/cmd/commands/accountscmd/funcs.go
index 0758a8244..5cefc5b51 100644
--- a/internal/cmd/commands/accountscmd/funcs.go
+++ b/internal/cmd/commands/accountscmd/funcs.go
@@ -9,6 +9,7 @@ import (
 	"github.com/hashicorp/boundary/api"
 	"github.com/hashicorp/boundary/api/accounts"
 	"github.com/hashicorp/boundary/internal/cmd/base"
+	"github.com/hashicorp/go-secure-stdlib/parseutil"
 	"github.com/hashicorp/go-secure-stdlib/password"
 	"github.com/hashicorp/go-secure-stdlib/strutil"
 )
@@ -116,59 +117,92 @@ func extraFlagsFuncImpl(c *Command, _ *base.FlagSets, f *base.FlagSet) {
 }
 
 func extraFlagsHandlingFuncImpl(c *Command, _ *base.FlagSets, opts *[]accounts.Option) bool {
-	if strutil.StrListContains(flagsMap[c.Func], "password") && c.flagPassword == "" {
-		fmt.Print("Password is not set as flag, please enter it now (will be hidden): ")
-		value, err := password.Read(os.Stdin)
-		fmt.Print("\n")
-		if err != nil {
-			c.UI.Error(fmt.Sprintf("An error occurred attempting to read the password. The raw error message is shown below but usually this is because you attempted to pipe a value into the command or you are executing outside of a terminal (TTY). The raw error was:\n\n%s", err.Error()))
-			return false
+	if strutil.StrListContains(flagsMap[c.Func], "password") {
+		switch c.flagPassword {
+		case "":
+			fmt.Print("Password is not set as flag, please enter it now (will be hidden): ")
+			value, err := password.Read(os.Stdin)
+			fmt.Print("\n")
+			if err != nil {
+				c.UI.Error(fmt.Sprintf("An error occurred attempting to read the password. The raw error message is shown below but usually this is because you attempted to pipe a value into the command or you are executing outside of a terminal (TTY). The raw error was:\n\n%s", err.Error()))
+				return false
+			}
+			fmt.Print("Please enter it one more time for confirmation: ")
+			confirmation, err := password.Read(os.Stdin)
+			fmt.Print("\n")
+			if err != nil {
+				c.UI.Error(fmt.Sprintf("An error occurred attempting to read the password. The raw error message is shown below but usually this is because you attempted to pipe a value into the command or you are executing outside of a terminal (TTY). The raw error was:\n\n%s", err.Error()))
+				return false
+			}
+			if strings.TrimSpace(value) != strings.TrimSpace(confirmation) {
+				c.UI.Error("Entered password and confirmation value did not match.")
+				return false
+			}
+			c.flagPassword = strings.TrimSpace(value)
+
+		default:
+			password, err := parseutil.ParsePath(c.flagPassword)
+			if err != nil && err.Error() != parseutil.ErrNotAUrl.Error() {
+				c.UI.Error(fmt.Sprintf("Error parsing password flag: %v", err))
+				return false
+			}
+			c.flagPassword = password
 		}
-		fmt.Print("Please enter it one more time for confirmation: ")
-		confirmation, err := password.Read(os.Stdin)
-		fmt.Print("\n")
-		if err != nil {
-			c.UI.Error(fmt.Sprintf("An error occurred attempting to read the password. The raw error message is shown below but usually this is because you attempted to pipe a value into the command or you are executing outside of a terminal (TTY). The raw error was:\n\n%s", err.Error()))
-			return false
-		}
-		if strings.TrimSpace(value) != strings.TrimSpace(confirmation) {
-			c.UI.Error("Entered password and confirmation value did not match.")
-			return false
-		}
-		c.flagPassword = strings.TrimSpace(value)
 	}
 
-	if strutil.StrListContains(flagsMap[c.Func], "current-password") && c.flagCurrentPassword == "" {
-		fmt.Print("Current password is not set as flag, please enter it now (will be hidden): ")
-		value, err := password.Read(os.Stdin)
-		fmt.Print("\n")
-		if err != nil {
-			c.UI.Error(fmt.Sprintf("An error occurred attempting to read the password. The raw error message is shown below but usually this is because you attempted to pipe a value into the command or you are executing outside of a terminal (TTY). The raw error was:\n\n%s", err.Error()))
-			return false
+	if strutil.StrListContains(flagsMap[c.Func], "current-password") {
+		switch c.flagCurrentPassword {
+		case "":
+			fmt.Print("Current password is not set as flag, please enter it now (will be hidden): ")
+			value, err := password.Read(os.Stdin)
+			fmt.Print("\n")
+			if err != nil {
+				c.UI.Error(fmt.Sprintf("An error occurred attempting to read the password. The raw error message is shown below but usually this is because you attempted to pipe a value into the command or you are executing outside of a terminal (TTY). The raw error was:\n\n%s", err.Error()))
+				return false
+			}
+			fmt.Print("Please enter it one more time for confirmation: ")
+			c.flagCurrentPassword = strings.TrimSpace(value)
+
+		default:
+			password, err := parseutil.ParsePath(c.flagCurrentPassword)
+			if err != nil && err.Error() != parseutil.ErrNotAUrl.Error() {
+				c.UI.Error(fmt.Sprintf("Error parsing current password flag: %v", err))
+				return false
+			}
+			c.flagCurrentPassword = password
 		}
-		fmt.Print("Please enter it one more time for confirmation: ")
-		confirmation, err := password.Read(os.Stdin)
-		fmt.Print("\n")
-		if err != nil {
-			c.UI.Error(fmt.Sprintf("An error occurred attempting to read the password. The raw error message is shown below but usually this is because you attempted to pipe a value into the command or you are executing outside of a terminal (TTY). The raw error was:\n\n%s", err.Error()))
-			return false
-		}
-		if strings.TrimSpace(value) != strings.TrimSpace(confirmation) {
-			c.UI.Error("Entered password and confirmation value did not match.")
-			return false
-		}
-		c.flagCurrentPassword = strings.TrimSpace(value)
 	}
 
-	if strutil.StrListContains(flagsMap[c.Func], "new-password") && c.flagNewPassword == "" {
-		fmt.Print("New password is not set as flag, please enter it now (will be hidden): ")
-		value, err := password.Read(os.Stdin)
-		fmt.Print("\n")
-		if err != nil {
-			c.UI.Error(fmt.Sprintf("An error occurred attempting to read the password. The raw error message is shown below but usually this is because you attempted to pipe a value into the command or you are executing outside of a terminal (TTY). The raw error was:\n\n%s", err.Error()))
-			return false
+	if strutil.StrListContains(flagsMap[c.Func], "new-password") {
+		switch c.flagNewPassword {
+		case "":
+			fmt.Print("New password is not set as flag, please enter it now (will be hidden): ")
+			value, err := password.Read(os.Stdin)
+			fmt.Print("\n")
+			if err != nil {
+				c.UI.Error(fmt.Sprintf("An error occurred attempting to read the password. The raw error message is shown below but usually this is because you attempted to pipe a value into the command or you are executing outside of a terminal (TTY). The raw error was:\n\n%s", err.Error()))
+				return false
+			}
+			confirmation, err := password.Read(os.Stdin)
+			fmt.Print("\n")
+			if err != nil {
+				c.UI.Error(fmt.Sprintf("An error occurred attempting to read the password. The raw error message is shown below but usually this is because you attempted to pipe a value into the command or you are executing outside of a terminal (TTY). The raw error was:\n\n%s", err.Error()))
+				return false
+			}
+			if strings.TrimSpace(value) != strings.TrimSpace(confirmation) {
+				c.UI.Error("Entered password and confirmation value did not match.")
+				return false
+			}
+			c.flagNewPassword = strings.TrimSpace(value)
+
+		default:
+			password, err := parseutil.ParsePath(c.flagNewPassword)
+			if err != nil && err.Error() != parseutil.ErrNotAUrl.Error() {
+				c.UI.Error(fmt.Sprintf("Error parsing new password flag: %v", err))
+				return false
+			}
+			c.flagNewPassword = password
 		}
-		c.flagNewPassword = strings.TrimSpace(value)
 	}
 
 	return true
diff --git a/internal/cmd/commands/accountscmd/password_funcs.go b/internal/cmd/commands/accountscmd/password_funcs.go
index 165d9da79..617614cb2 100644
--- a/internal/cmd/commands/accountscmd/password_funcs.go
+++ b/internal/cmd/commands/accountscmd/password_funcs.go
@@ -7,6 +7,7 @@ import (
 
 	"github.com/hashicorp/boundary/api/accounts"
 	"github.com/hashicorp/boundary/internal/cmd/base"
+	"github.com/hashicorp/go-secure-stdlib/parseutil"
 	"github.com/hashicorp/go-secure-stdlib/password"
 	"github.com/hashicorp/go-secure-stdlib/strutil"
 )
@@ -72,7 +73,7 @@ func extraPasswordFlagsFuncImpl(c *PasswordCommand, set *base.FlagSets, f *base.
 			f.StringVar(&base.StringVar{
 				Name:   "password",
 				Target: &c.flagPassword,
-				Usage:  "The password for the account. If not specified, the command will prompt for the password to be entered in a non-echoing way.",
+				Usage:  "The password for the account. If blank, the command will prompt for the password to be entered interactively in a non-echoing way. Otherwise, this can refer to a file on disk (file://) from which a password will be read; an env var (env://) from which the password will be read; or a string containing the password.",
 			})
 		}
 	}
@@ -114,8 +115,14 @@ func extraPasswordFlagsHandlingFuncImpl(c *PasswordCommand, _ *base.FlagSets, op
 				return false
 			}
 			*opts = append(*opts, accounts.WithPasswordAccountPassword(strings.TrimSpace(value)))
+
 		default:
-			*opts = append(*opts, accounts.WithPasswordAccountPassword(c.flagPassword))
+			password, err := parseutil.ParsePath(c.flagPassword)
+			if err != nil && err.Error() != parseutil.ErrNotAUrl.Error() {
+				c.UI.Error(fmt.Sprintf("Error parsing password flag: %v", err))
+				return false
+			}
+			*opts = append(*opts, accounts.WithPasswordAccountPassword(password))
 		}
 	}
 
diff --git a/internal/cmd/commands/authenticate/password.go b/internal/cmd/commands/authenticate/password.go
index 6e14b07cd..f9f91414f 100644
--- a/internal/cmd/commands/authenticate/password.go
+++ b/internal/cmd/commands/authenticate/password.go
@@ -9,6 +9,7 @@ import (
 	"github.com/hashicorp/boundary/api"
 	"github.com/hashicorp/boundary/api/authmethods"
 	"github.com/hashicorp/boundary/internal/cmd/base"
+	"github.com/hashicorp/go-secure-stdlib/parseutil"
 	"github.com/hashicorp/go-secure-stdlib/password"
 	"github.com/mitchellh/cli"
 	"github.com/mitchellh/go-wordwrap"
@@ -56,21 +57,21 @@ func (c *PasswordCommand) Flags() *base.FlagSets {
 		Name:   "login-name",
 		Target: &c.flagLoginName,
 		EnvVar: envLoginName,
-		Usage:  "The login name corresponding to an account within the given auth method",
+		Usage:  "The login name corresponding to an account within the given auth method.",
 	})
 
 	f.StringVar(&base.StringVar{
 		Name:   "password",
 		Target: &c.flagPassword,
 		EnvVar: envPassword,
-		Usage:  "The password associated with the login name",
+		Usage:  "The password associated with the login name. If blank, the command will prompt for the password to be entered interactively in a non-echoing way. Otherwise, this can refer to a file on disk (file://) from which a password will be read; an env var (env://) from which the password will be read; or a string containing the password.",
 	})
 
 	f.StringVar(&base.StringVar{
 		Name:   "auth-method-id",
 		EnvVar: "BOUNDARY_AUTH_METHOD_ID",
 		Target: &c.FlagAuthMethodId,
-		Usage:  "The auth-method resource to use for the operation",
+		Usage:  "The auth-method resource to use for the operation.",
 	})
 
 	return set
@@ -101,7 +102,8 @@ func (c *PasswordCommand) Run(args []string) int {
 		return base.CommandUserError
 	}
 
-	if c.flagPassword == "" {
+	switch c.flagPassword {
+	case "":
 		fmt.Print("Password is not set as flag or in env, please enter it now (will be hidden): ")
 		value, err := password.Read(os.Stdin)
 		fmt.Print("\n")
@@ -110,6 +112,14 @@ func (c *PasswordCommand) Run(args []string) int {
 			return base.CommandUserError
 		}
 		c.flagPassword = strings.TrimSpace(value)
+
+	default:
+		password, err := parseutil.ParsePath(c.flagPassword)
+		if err != nil && err.Error() != parseutil.ErrNotAUrl.Error() {
+			c.UI.Error(fmt.Sprintf("Error parsing password flag: %v", err))
+			return base.CommandUserError
+		}
+		c.flagPassword = password
 	}
 
 	client, err := c.Client(base.WithNoTokenScope(), base.WithNoTokenValue())