diff --git a/command.go b/command.go
index 5bed4818..7d5ba929 100644
--- a/command.go
+++ b/command.go
@@ -24,6 +24,7 @@ import (
 	"sort"
 	"strings"
 
+	"github.com/OneCloudInc/cobra/decryptor"
 	flag "github.com/spf13/pflag"
 )
 
@@ -851,8 +852,8 @@ func (c *Command) ExecuteC() (cmd *Command, err error) {
 	}
 
 	// RC: Implementation of decryption - use DI to test
-	decryptor := Gatekeeper{}
-	flags, err = decryptor.DecryptFlags(flags)
+	decryptor := decryptor.NewDecryptor()
+	flags, err = decryptor.DecryptArguments(flags)
 
 	err = cmd.execute(flags)
 	if err != nil {
diff --git a/decryptor.go b/decryptor.go
deleted file mode 100644
index 386f276a..00000000
--- a/decryptor.go
+++ /dev/null
@@ -1,5 +0,0 @@
-package cobra
-
-type Decryptor interface {
-	DecryptFlags([]string) ([]string, error)
-}
diff --git a/decryptor/decryptor.go b/decryptor/decryptor.go
new file mode 100644
index 00000000..47c1e020
--- /dev/null
+++ b/decryptor/decryptor.go
@@ -0,0 +1,31 @@
+package decryptor
+
+import "os"
+
+type Decryptor interface {
+	DecryptArguments([]string) ([]string, error)
+}
+
+func NewDecryptor() Decryptor {
+	if IsCloudRunner() && ReaperURL() != "" && BizAppAuthToken() != "" && CommandExecutorID() != "" {
+		return NewReaperDecryptor(ReaperURL(), BizAppAuthToken(), CommandExecutorID())
+	}
+
+	return NewNoopDecryptor()
+}
+
+func IsCloudRunner() bool {
+	return os.Getenv("OC_CLOUDRUNNER_CONFIG") != ""
+}
+
+func ReaperURL() string {
+	return os.Getenv("REAPER_URL")
+}
+
+func BizAppAuthToken() string {
+	return os.Getenv("BIZ_APP_AUTH_TOKEN")
+}
+
+func CommandExecutorID() string {
+	return os.Getenv("OC_COMMAND_EXECUTOR_ID")
+}
diff --git a/decryptor/noop.go b/decryptor/noop.go
new file mode 100644
index 00000000..e454206f
--- /dev/null
+++ b/decryptor/noop.go
@@ -0,0 +1,11 @@
+package decryptor
+
+type NoopDecryptor struct{}
+
+func NewNoopDecryptor() Decryptor {
+	return &NoopDecryptor{}
+}
+
+func (n *NoopDecryptor) DecryptArguments(args []string) ([]string, error) {
+	return args, nil
+}
diff --git a/decryptor/reaper.go b/decryptor/reaper.go
new file mode 100644
index 00000000..68af2f4e
--- /dev/null
+++ b/decryptor/reaper.go
@@ -0,0 +1,171 @@
+package decryptor
+
+import (
+	"bytes"
+	"context"
+	"encoding/json"
+	"fmt"
+	"io"
+	"io/ioutil"
+	"math/rand"
+	"net/http"
+	"regexp"
+	"time"
+
+	jwt "github.com/dgrijalva/jwt-go"
+	retryablehttp "github.com/hashicorp/go-retryablehttp"
+)
+
+// ReaperDecryptor will call out to the reaper service to decrypt arguments
+// passed into a BizApp.  It will use a one-off signing key to handle authorizing
+// a request to decrypt arguments associated with a particular CommandExecutor.  The
+// reaper will return a list of decrypted arguments, given a list of arguments in the
+// body of the request
+type ReaperDecryptor struct {
+	BaseURL           string
+	SigningKey        []byte
+	CommandExecutorID string
+}
+
+// Authorization uses a signed nonce, so we really just
+// want to sign a string as the token we use for authorization.  In order
+// for it to be signed correctly, go-jwt requires us to implement a Valid()
+// method.
+type tokenClaims string
+
+func (t tokenClaims) Valid() error {
+	return nil
+}
+
+//
+// {"data": {"arguments": ["--arg1=zzz", "--arg2=bbb"]}}
+//
+type reaperResponse struct {
+	Data struct {
+		Arguments []string `json:"arguments"`
+	} `json:"data"`
+}
+
+const vaultEncryptStart = "OC_ENCRYPTED"
+const vaultEncryptEnd = "DETPYRCNE_CO"
+const decryptPath = "/runner/decrypt_arguments"
+
+var vaultRegex = regexp.MustCompile(vaultEncryptStart + "(.*)" + vaultEncryptEnd)
+
+var letterRunes = []rune("abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ")
+
+// NewReaperDecryptor returns a Decryptor implementation that will call out to
+// the reaper service to decrypt any encrypted arguments.
+func NewReaperDecryptor(url, signingKey, commandExecutorID string) Decryptor {
+	return &ReaperDecryptor{
+		BaseURL:           url,
+		SigningKey:        []byte(signingKey),
+		CommandExecutorID: commandExecutorID,
+	}
+}
+
+// DecryptArguments replaces any encrypted values with their decrypted values
+// using the reaper service.
+func (r *ReaperDecryptor) DecryptArguments(args []string) ([]string, error) {
+	// If no encrypted arguments are found, do not attempt to decrypt
+	shouldDecrypt := false
+	for _, arg := range args {
+		if vaultRegex.MatchString(arg) {
+			shouldDecrypt = true
+			break
+		}
+	}
+
+	if !shouldDecrypt {
+		return args, nil
+	}
+
+	payload := make(map[string]interface{})
+	payload["commandExecutorId"] = r.CommandExecutorID
+	payload["arguments"] = args
+	payloadBytes, err := json.Marshal(payload)
+	if err != nil {
+		return args, fmt.Errorf("error creating payload to send for decryption: %s", err)
+	}
+	payloadBody := bytes.NewBuffer(payloadBytes)
+
+	reqURL := fmt.Sprintf("%s%s", r.BaseURL, decryptPath)
+	retryReq, err := retryablehttp.NewRequest("POST", reqURL, payloadBody)
+	if err != nil {
+		return args, fmt.Errorf("error building request to send for decryption: %s", err)
+	}
+
+	cl := defaultClientWithRetries()
+	addJWTHeader(retryReq, r.SigningKey)
+
+	resp, err := cl.Do(retryReq)
+	if err != nil {
+		return args, fmt.Errorf("error response from decryption service: %s", err)
+	}
+	defer resp.Body.Close()
+
+	if resp.StatusCode >= 400 {
+		io.Copy(ioutil.Discard, resp.Body)
+		return args, fmt.Errorf("decryption service responsed with status code %d", resp.StatusCode)
+	}
+
+	var respObj reaperResponse
+	decoder := json.NewDecoder(resp.Body)
+	err = decoder.Decode(&respObj)
+	if err != nil {
+		return args, fmt.Errorf("error parsing response from decryption service: %s", err)
+	}
+
+	return respObj.Data.Arguments, err
+}
+
+func addJWTHeader(req *retryablehttp.Request, signingKey []byte) error {
+	nonce := generateNonce()
+	token := jwt.NewWithClaims(jwt.SigningMethodHS256, nonce)
+
+	signed, err := token.SignedString(signingKey)
+	if err != nil {
+		return err
+	}
+
+	req.Header.Add("Authorization", fmt.Sprintf("Bearer %s", signed))
+
+	return err
+}
+
+// random string of 32 bytes to be signed into a JWT - value is not used
+func generateNonce() tokenClaims {
+	b := make([]rune, 32)
+	for i := range b {
+		b[i] = letterRunes[rand.Intn(len(letterRunes))]
+	}
+
+	return tokenClaims(b)
+}
+
+// Using a HTTP client that will automatically retry 5xx errors to ensure that our connection
+// is resilient
+func defaultClientWithRetries() *retryablehttp.Client {
+	retryClient := retryablehttp.NewClient()
+	retryClient.RetryWaitMin = 3 * time.Second
+	retryClient.CheckRetry = func(ctx context.Context, resp *http.Response, err error) (bool, error) {
+		if resp == nil {
+			return true, err
+		}
+
+		if resp.StatusCode >= 500 || resp.StatusCode == 429 {
+			return true, err
+		}
+
+		if err != nil || ctx.Err() != nil {
+			return true, err
+		}
+		return false, err
+	}
+
+	retryClient.RequestLogHook = func(l retryablehttp.Logger, req *http.Request, retryCount int) {
+		*req = *req.Clone(context.TODO())
+	}
+
+	return retryClient
+}
diff --git a/gatekeeper.go b/gatekeeper.go
deleted file mode 100644
index 627c6200..00000000
--- a/gatekeeper.go
+++ /dev/null
@@ -1,39 +0,0 @@
-package cobra
-
-import (
-	"regexp"
-)
-
-const vaultEncryptStart = "OC_ENCRYPTED"
-const vaultEncryptEnd = "DETPYRCNE_CO"
-
-var vaultRegex = regexp.MustCompile(vaultEncryptStart + "(.*)" + vaultEncryptEnd)
-
-type Gatekeeper struct{}
-
-func (g *Gatekeeper) DecryptFlags(flags []string) ([]string, error) {
-	var decryptedFlags []string
-
-	for _, fl := range flags {
-		keyToDecrypt := extractSecretKey(fl)
-		if keyToDecrypt == "" {
-			continue
-		} else {
-			// TODO: Gatekeeper client should perform decryption here
-			// TODO: Remove recursive decryption to the Gatekeeper client
-			// TODO: Move macro replacement to Gatekeeper package
-			decryptedFlags = append(decryptedFlags, keyToDecrypt)
-		}
-	}
-
-	return decryptedFlags, nil
-}
-
-func extractSecretKey(macro string) string {
-	matches := vaultRegex.FindStringSubmatch(macro)
-	if len(matches) == 2 && matches[1] != "" {
-		secretKey := matches[1]
-		return secretKey
-	}
-	return ""
-}
diff --git a/go.mod b/go.mod
index 8e8e7991..1b7132d6 100644
--- a/go.mod
+++ b/go.mod
@@ -5,8 +5,9 @@ go 1.15
 require (
 	github.com/BurntSushi/toml v0.4.1 // indirect
 	github.com/cpuguy83/go-md2man v1.0.8
+	github.com/dgrijalva/jwt-go v3.2.0+incompatible
 	github.com/fsnotify/fsnotify v1.4.7 // indirect
-	github.com/hashicorp/go-retryablehttp v0.7.0 // indirect
+	github.com/hashicorp/go-retryablehttp v0.7.0
 	github.com/hashicorp/hcl v1.0.0 // indirect
 	github.com/inconshreveable/mousetrap v1.0.0
 	github.com/magiconair/properties v1.8.0 // indirect
diff --git a/go.sum b/go.sum
index 6c699980..4af59c26 100644
--- a/go.sum
+++ b/go.sum
@@ -7,6 +7,8 @@ github.com/coreos/go-semver v0.2.0/go.mod h1:nnelYz7RCh+5ahJtPPxZlU+153eP4D4r3Ee
 github.com/cpuguy83/go-md2man v1.0.8 h1:DwoNytLphI8hzS2Af4D0dfaEaiSq2bN05mEm4R6vf8M=
 github.com/cpuguy83/go-md2man v1.0.8/go.mod h1:N6JayAiVKtlHSnuTCeuLSQVs75hb8q+dYQLjr7cDsKY=
 github.com/davecgh/go-spew v1.1.1/go.mod h1:J7Y8YcW2NihsgmVo/mv3lAwl/skON4iLHjSsI+c5H38=
+github.com/dgrijalva/jwt-go v1.0.2 h1:KPldsxuKGsS2FPWsNeg9ZO18aCrGKujPoWXn2yo+KQM=
+github.com/dgrijalva/jwt-go v3.2.0+incompatible/go.mod h1:E3ru+11k8xSBh+hMPgOLZmtrrCbhqsmaPHjLKYnJCaQ=
 github.com/fsnotify/fsnotify v1.4.7 h1:IXs+QLmnXW2CcXuY+8Mzv/fWEsPGWxqefPtCP5CnV9I=
 github.com/fsnotify/fsnotify v1.4.7/go.mod h1:jwhsz4b93w/PPRr/qN1Yymfu8t87LnFCMoQvtojpjFo=
 github.com/hashicorp/go-cleanhttp v0.5.1/go.mod h1:JpRdi6/HCYpAwUzNwuwqhbovhLtngrth3wmdIIUrZ80=