diff --git a/command/ca/bootstrap.go b/command/ca/bootstrap.go
index a1c3c7b4..71bab078 100644
--- a/command/ca/bootstrap.go
+++ b/command/ca/bootstrap.go
@@ -75,14 +75,8 @@ domain name 'certs.example-team.ca.smallstep.com' the value would be 'certs'.`,
 			flags.TeamURL,
 			flags.RedirectURL,
 			flags.Force,
-			cli.StringFlag{
-				Name:  "context-name",
-				Usage: `The <string> that will serve as the key for the context.`,
-			},
-			cli.StringFlag{
-				Name:  "context-profile",
-				Usage: `The <string> that will serve as the profile name for the context.`,
-			},
+			flags.ContextName,
+			flags.ContextProfile,
 		},
 	}
 }
diff --git a/command/ca/init.go b/command/ca/init.go
index a6ed14aa..1450a641 100644
--- a/command/ca/init.go
+++ b/command/ca/init.go
@@ -7,6 +7,8 @@ import (
 	"fmt"
 	"io"
 	"os"
+	"path/filepath"
+	"regexp"
 	"strings"
 	"time"
 
@@ -15,6 +17,7 @@ import (
 	"github.com/smallstep/certificates/kms"
 	"github.com/smallstep/certificates/pki"
 	"github.com/smallstep/cli/crypto/pemutil"
+	"github.com/smallstep/cli/flags"
 	"github.com/smallstep/cli/ui"
 	"github.com/smallstep/cli/utils"
 	"github.com/urfave/cli"
@@ -24,6 +27,7 @@ import (
 
 	"go.step.sm/cli-utils/command"
 	"go.step.sm/cli-utils/errs"
+	"go.step.sm/cli-utils/step"
 )
 
 func initCommand() cli.Command {
@@ -36,7 +40,8 @@ func initCommand() cli.Command {
 [**--helm**] [**--deployment-type**=<name>] [**--name**=<name>]
 [**--dns**=<dns>] [**--address**=<address>] [**--provisioner**=<name>]
 [**--provisioner-password-file**=<file>] [**--password-file**=<file>]
-[**--with-ca-url**=<url>] [**--ra**=<type>] [**--kms**=<type>] [**--no-db**]`,
+[**--ra**=<type>] [**--kms**=<type>] [**--with-ca-url**=<url>] [**--no-db**]
+[**--context-name**=<string>] [**--context-profile**=<string>]`,
 		Description: `**step ca init** command initializes a public key infrastructure (PKI) to be
  used by the Certificate Authority.`,
 		Flags: []cli.Flag{
@@ -163,6 +168,8 @@ Cloud.`,
 				Name:  "no-db",
 				Usage: `Generate a CA configuration without the DB stanza. No persistence layer.`,
 			},
+			flags.ContextName,
+			flags.ContextProfile,
 		},
 	}
 }
@@ -439,6 +446,40 @@ func initAction(ctx *cli.Context) (err error) {
 			IsCreator:  true,
 			KeyManager: keyManager,
 		}
+
+	}
+
+	// Set appropriate context.
+	fi, err := os.Stat(filepath.Join(step.BasePath(), "config"))
+	configDirExists := !os.IsNotExist(err) && fi.IsDir()
+	fi, err = os.Stat(filepath.Join(step.BasePath(), "authorities"))
+	authoritiesDirExists := !os.IsNotExist(err) && fi.IsDir()
+
+	if !configDirExists || authoritiesDirExists {
+		reg, err := regexp.Compile("[^a-zA-Z0-9]+")
+		if err != nil {
+			return err
+		}
+		processedName := strings.ToLower(strings.ReplaceAll(reg.ReplaceAllString(name, ""), " ", "-"))
+
+		contextName := ctx.String("context-name")
+		if contextName == "" {
+			contextName = processedName
+		}
+		contextProfile := ctx.String("context-profile")
+		if contextProfile == "" {
+			contextProfile = processedName
+		}
+		if err := step.AddContext(&step.Context{
+			Name:      contextName,
+			Profile:   contextProfile,
+			Authority: processedName,
+		}); err != nil {
+			return err
+		}
+		if err := step.SwitchCurrentContext(contextName); err != nil {
+			return err
+		}
 	}
 
 	if pkiOnly {
diff --git a/command/context/select.go b/command/context/select.go
index c4167178..fa51e422 100644
--- a/command/context/select.go
+++ b/command/context/select.go
@@ -1,14 +1,9 @@
 package context
 
 import (
-	"encoding/json"
-
-	"github.com/pkg/errors"
 	"github.com/smallstep/cli/ui"
 	"github.com/urfave/cli"
 	"go.step.sm/cli-utils/command"
-	"go.step.sm/cli-utils/errs"
-	"go.step.sm/cli-utils/fileutil"
 	"go.step.sm/cli-utils/step"
 )
 
@@ -37,23 +32,10 @@ $ step context select alpha-one
 }
 
 func selectAction(ctx *cli.Context) error {
-	ctxStr := ctx.Args().Get(0)
-	if _, ok := step.GetContext(ctxStr); !ok {
-		return errors.Errorf("context '%s' not found", ctxStr)
-	}
-
-	type currentCtxType struct {
-		Context string `json:"context"`
-	}
-	def := currentCtxType{Context: ctxStr}
-	b, err := json.Marshal(def)
-	if err != nil {
+	name := ctx.Args().Get(0)
+	if err := step.WriteCurrentContext(name); err != nil {
 		return err
 	}
-	ctx.Set("force", "true")
-	if err = fileutil.WriteFile(step.CurrentContextFile(), b, 0644); err != nil {
-		return errs.FileError(err, step.CurrentContextFile())
-	}
-	ui.PrintSelected("Context", ctxStr)
+	ui.PrintSelected("Context", name)
 	return nil
 }
diff --git a/command/ssh/config.go b/command/ssh/config.go
index 8295daa0..5760a6ca 100644
--- a/command/ssh/config.go
+++ b/command/ssh/config.go
@@ -22,7 +22,8 @@ func configCommand() cli.Command {
 [**--team**=<name>] [**--host**] [**--set**=<key=value>] [**--set-file**=<file>]
 [**--dry-run**] [**--roots**] [**--federation**] [**--force**]
 [**--offline**] [**--ca-config**=<file>]
-[**--ca-url**=<uri>] [**--root**=<file>] [**--context**=<context]`,
+[**--ca-url**=<uri>] [**--root**=<file>] [**--context**=<context]
+[**--context-name**=<string>] [**--context-profile**=<string>]`,
 		Description: `**step ssh config** configures SSH to be used with certificates. It also supports
 flags to inspect the root certificates used to sign the certificates.
 
@@ -84,14 +85,8 @@ times to set multiple variables.`,
 			flags.Root,
 			flags.Offline,
 			flags.Context,
-			cli.StringFlag{
-				Name:  "context-name",
-				Usage: `The <string> that will serve as the key for the context.`,
-			},
-			cli.StringFlag{
-				Name:  "context-profile",
-				Usage: `The <string> that will serve as the profile name for the context.`,
-			},
+			flags.ContextName,
+			flags.ContextProfile,
 		},
 	}
 }
@@ -107,6 +102,10 @@ func configAction(ctx *cli.Context) (recoverErr error) {
 	isFederation := ctx.Bool("federation")
 	sets := ctx.StringSlice("set")
 
+	context := ctx.String("context")
+	contextName := ctx.String("context-name")
+	contextProfile := ctx.String("context-profile")
+
 	switch {
 	case team != "" && isHost:
 		return errs.IncompatibleFlagWithFlag(ctx, "team", "host")
@@ -116,12 +115,18 @@ func configAction(ctx *cli.Context) (recoverErr error) {
 		return errs.IncompatibleFlagWithFlag(ctx, "team", "federation")
 	case team != "" && len(sets) > 0:
 		return errs.IncompatibleFlagWithFlag(ctx, "team", "set")
+	case team != "" && context != "":
+		return errs.IncompatibleFlagWithFlag(ctx, "team", "context")
 	case isRoots && isFederation:
 		return errs.IncompatibleFlagWithFlag(ctx, "roots", "federation")
 	case isRoots && len(sets) > 0:
 		return errs.IncompatibleFlagWithFlag(ctx, "roots", "set")
 	case isFederation && len(sets) > 0:
 		return errs.IncompatibleFlagWithFlag(ctx, "federation", "set")
+	case context != "" && contextName != "":
+		return errs.IncompatibleFlagWithFlag(ctx, "context", "context-name")
+	case context != "" && contextProfile != "":
+		return errs.IncompatibleFlagWithFlag(ctx, "context", "context-profile")
 	}
 
 	// Bootstrap Authority
@@ -135,15 +140,18 @@ func configAction(ctx *cli.Context) (recoverErr error) {
 	args = append(args, os.Args[3:]...)
 
 	if step.IsContextEnabled() {
-		ctxName := ctx.String("context-name")
-		if ctxName == "" {
-			ctxName = "ssh." + team
+		switch {
+		case context != "":
+			args = append(args, "--context", context)
+		case team != "" && contextName != "":
+			args = append(args, "--context", contextName)
+		case team != "":
+			args = append(args, "--context", "ssh."+team)
 		}
-		args = append(args, "--context", ctxName)
 	}
 
 	if _, err := exec.Step(args...); err != nil {
-		return errors.Wrap(err, "error configuring ssh authority")
+		return errors.Wrap(err, "error configuring ssh")
 	}
 	return nil
 }
diff --git a/command/ssh/configHelper.go b/command/ssh/configHelper.go
index 97579724..f7a2a4d3 100644
--- a/command/ssh/configHelper.go
+++ b/command/ssh/configHelper.go
@@ -2,7 +2,6 @@ package ssh
 
 import (
 	"encoding/base64"
-	"fmt"
 	"net/http"
 	"runtime"
 	"strings"
@@ -171,7 +170,7 @@ func configHelperAction(ctx *cli.Context) (recoverErr error) {
 		}
 
 		for _, key := range keys {
-			fmt.Printf("%s %s\n", key.Type(), base64.StdEncoding.EncodeToString(key.Marshal()))
+			ui.Printf("%s %s\n", key.Type(), base64.StdEncoding.EncodeToString(key.Marshal()))
 		}
 		return nil
 	}
@@ -241,7 +240,7 @@ func configHelperAction(ctx *cli.Context) (recoverErr error) {
 		templates = resp.UserTemplates
 	}
 	if len(templates) == 0 {
-		fmt.Println("No configuration changes were found.")
+		ui.Println("No configuration changes were found.")
 		return nil
 	}
 
@@ -258,7 +257,7 @@ func configHelperAction(ctx *cli.Context) (recoverErr error) {
 	if ctx.Bool("dry-run") {
 		for _, t := range templates {
 			ui.Printf("{{ \"%s\" | bold }}\n", step.Abs(t.Path))
-			fmt.Println(string(t.Content))
+			ui.Println(string(t.Content))
 		}
 		return nil
 	}
diff --git a/flags/flags.go b/flags/flags.go
index 3bd56015..5afe2417 100644
--- a/flags/flags.go
+++ b/flags/flags.go
@@ -192,6 +192,18 @@ generating key.`,
 		Usage: "The <context> to apply before running the given command.",
 	}
 
+	// ContextName the name to use as the key for a new Context.
+	ContextName = cli.StringFlag{
+		Name:  "context-name",
+		Usage: `The <string> that will serve as the key for the context.`,
+	}
+
+	// ContextProfile the profile name to use for a new Context.
+	ContextProfile = cli.StringFlag{
+		Name:  "context-profile",
+		Usage: `The <string> that will serve as the profile name for the context.`,
+	}
+
 	// Offline is a cli.Flag used to activate the offline flow.
 	Offline = cli.BoolFlag{
 		Name: "offline",