diff --git a/config/config_test.go b/config/config_test.go
index abf2c66a5..805b31699 100644
--- a/config/config_test.go
+++ b/config/config_test.go
@@ -94,6 +94,9 @@ creation_rules:
     - kms:
       - arn: foo
         aws_profile: bar
+      - arn: foo
+        context:
+          baz: bam
       pgp:
       - bar
       gcp_kms:
@@ -421,6 +424,7 @@ func TestLoadConfigFile(t *testing.T) {
 }
 
 func TestLoadConfigFileWithGroups(t *testing.T) {
+	bam := "bam"
 	expected := configFile{
 		CreationRules: []creationRule{
 			{
@@ -432,7 +436,18 @@ func TestLoadConfigFileWithGroups(t *testing.T) {
 				PathRegex: "",
 				KeyGroups: []keyGroup{
 					{
-						KMS:     []kmsKey{{Arn: "foo", AwsProfile: "bar"}},
+						KMS: []kmsKey{
+							{
+								Arn:        "foo",
+								AwsProfile: "bar",
+							},
+							{
+								Arn: "foo",
+								Context: map[string]*string{
+									"baz": &bam,
+								},
+							},
+						},
 						PGP:     []string{"bar"},
 						GCPKMS:  []gcpKmsKey{{ResourceID: "foo"}},
 						AzureKV: []azureKVKey{{VaultURL: "https://foo.vault.azure.net", Key: "foo-key", Version: "fooversion"}},
@@ -464,7 +479,7 @@ func TestLoadConfigFileWithMerge(t *testing.T) {
 	assert.Nil(t, err)
 	assert.Equal(t, 2, len(conf.KeyGroups))
 	assert.Equal(t, 1, len(conf.KeyGroups[0]))
-	assert.Equal(t, 22, len(conf.KeyGroups[1]))
+	assert.Equal(t, 23, len(conf.KeyGroups[1]))
 }
 
 func TestLoadConfigFileWithNoMatchingRules(t *testing.T) {
@@ -538,9 +553,10 @@ func TestKeyGroupsForFileWithGroups(t *testing.T) {
 	conf, err := parseCreationRuleForFile(parseConfigFile(sampleConfigWithGroups, t), "/conf/path", "whatever", nil)
 	assert.Nil(t, err)
 	assert.Equal(t, "bar", conf.KeyGroups[0][0].ToString())
-	assert.Equal(t, "foo", conf.KeyGroups[0][1].ToString())
+	assert.Equal(t, "foo||bar", conf.KeyGroups[0][1].ToString())
+	assert.Equal(t, "foo|baz:bam", conf.KeyGroups[0][2].ToString())
 	assert.Equal(t, "qux", conf.KeyGroups[1][0].ToString())
-	assert.Equal(t, "baz", conf.KeyGroups[1][1].ToString())
+	assert.Equal(t, "baz||foo", conf.KeyGroups[1][1].ToString())
 }
 
 func TestLoadConfigFileWithUnencryptedSuffix(t *testing.T) {
diff --git a/kms/keysource.go b/kms/keysource.go
index e1441b492..bf222c8b0 100644
--- a/kms/keysource.go
+++ b/kms/keysource.go
@@ -11,6 +11,7 @@ import (
 	"fmt"
 	"os"
 	"regexp"
+	"sort"
 	"strings"
 	"time"
 
@@ -181,6 +182,38 @@ func ParseKMSContext(in interface{}) map[string]*string {
 	return out
 }
 
+// kmsContextToString converts a dictionary into a string that can be parsed
+// again with ParseKMSContext().
+func kmsContextToString(in map[string]*string) string {
+	if len(in) == 0 {
+		return ""
+	}
+
+	// Collect the keys in a slice and compute the expected length
+	keys := make([]string, 0, len(in))
+	length := 0
+	for key := range in {
+		keys = append(keys, key)
+		length += len(key) + len(*in[key]) + 2
+	}
+
+	// Sort the keys
+	sort.Strings(keys)
+
+	// Compose a comma-separated string of key-vale pairs
+	var builder strings.Builder
+	builder.Grow(length)
+	for index, key := range keys {
+		if index > 0 {
+			builder.WriteString(",")
+		}
+		builder.WriteString(key)
+		builder.WriteByte(':')
+		builder.WriteString(*in[key])
+	}
+	return builder.String()
+}
+
 // CredentialsProvider is a wrapper around aws.CredentialsProvider used for
 // authentication towards AWS KMS.
 type CredentialsProvider struct {
@@ -278,7 +311,18 @@ func (key *MasterKey) NeedsRotation() bool {
 
 // ToString converts the key to a string representation.
 func (key *MasterKey) ToString() string {
-	return key.Arn
+	arnRole := key.Arn
+	if key.Role != "" {
+		arnRole = fmt.Sprintf("%s+%s", key.Arn, key.Role)
+	}
+	context := kmsContextToString(key.EncryptionContext)
+	if key.AwsProfile != "" {
+		return fmt.Sprintf("%s|%s|%s", arnRole, context, key.AwsProfile)
+	}
+	if len(key.EncryptionContext) > 0 {
+		return fmt.Sprintf("%s|%s", arnRole, context)
+	}
+	return arnRole
 }
 
 // ToMap converts the MasterKey to a map for serialization purposes.
diff --git a/kms/keysource_test.go b/kms/keysource_test.go
index a44ab1ec2..da3c6b51e 100644
--- a/kms/keysource_test.go
+++ b/kms/keysource_test.go
@@ -367,8 +367,38 @@ func TestMasterKey_NeedsRotation(t *testing.T) {
 }
 
 func TestMasterKey_ToString(t *testing.T) {
+	dummyARNWithRole := fmt.Sprintf("%s+arn:aws:iam::my-role", dummyARN)
+
+	bar := "bar"
+	bam := "bam"
+	context := map[string]*string{
+		"foo": &bar,
+		"baz": &bam,
+	}
+
 	key := NewMasterKeyFromArn(dummyARN, nil, "")
 	assert.Equal(t, dummyARN, key.ToString())
+
+	key = NewMasterKeyFromArn(dummyARNWithRole, nil, "")
+	assert.Equal(t, dummyARNWithRole, key.ToString())
+
+	key = NewMasterKeyFromArn(dummyARN, nil, "profile")
+	assert.Equal(t, fmt.Sprintf("%s||profile", dummyARN), key.ToString())
+
+	key = NewMasterKeyFromArn(dummyARNWithRole, nil, "profile")
+	assert.Equal(t, fmt.Sprintf("%s||profile", dummyARNWithRole), key.ToString())
+
+	key = NewMasterKeyFromArn(dummyARN, context, "")
+	assert.Equal(t, fmt.Sprintf("%s|baz:bam,foo:bar", dummyARN), key.ToString())
+
+	key = NewMasterKeyFromArn(dummyARNWithRole, context, "")
+	assert.Equal(t, fmt.Sprintf("%s|baz:bam,foo:bar", dummyARNWithRole), key.ToString())
+
+	key = NewMasterKeyFromArn(dummyARN, context, "profile")
+	assert.Equal(t, fmt.Sprintf("%s|baz:bam,foo:bar|profile", dummyARN), key.ToString())
+
+	key = NewMasterKeyFromArn(dummyARNWithRole, context, "profile")
+	assert.Equal(t, fmt.Sprintf("%s|baz:bam,foo:bar|profile", dummyARNWithRole), key.ToString())
 }
 
 func TestMasterKey_ToMap(t *testing.T) {