diff --git a/cmd/sops/common/common.go b/cmd/sops/common/common.go
index 7a52b8fcd..e684c2f0e 100644
--- a/cmd/sops/common/common.go
+++ b/cmd/sops/common/common.go
@@ -32,7 +32,7 @@ type DecryptTreeOpts struct {
 func DecryptTree(opts DecryptTreeOpts) (dataKey []byte, err error) {
 	dataKey, err = opts.Tree.Metadata.GetDataKeyWithKeyServices(opts.KeyServices)
 	if err != nil {
-		return nil, cli.NewExitError(err.Error(), codes.CouldNotRetrieveKey)
+		return nil, NewExitError(err, codes.CouldNotRetrieveKey)
 	}
 	computedMac, err := opts.Tree.Decrypt(dataKey, opts.Cipher)
 	if err != nil {
@@ -96,6 +96,13 @@ func LoadEncryptedFile(inputStore sops.Store, inputPath string) (*sops.Tree, err
 	return &tree, nil
 }
 
+func NewExitError(i interface{}, exitCode int) *cli.ExitError {
+	if userErr, ok := i.(sops.UserError); ok {
+		return cli.NewExitError(userErr.UserError(), exitCode)
+	}
+	return cli.NewExitError(i, exitCode)
+}
+
 func IsYAMLFile(path string) bool {
 	return strings.HasSuffix(path, ".yaml") || strings.HasSuffix(path, ".yml")
 }
diff --git a/sops.go b/sops.go
index ca824b774..95b4ae35c 100644
--- a/sops.go
+++ b/sops.go
@@ -435,35 +435,22 @@ func (m Metadata) GetDataKeyWithKeyServices(svcs []keyservice.KeyServiceClient)
 	if m.DataKey != nil {
 		return m.DataKey, nil
 	}
-	errMsg := "Could not decrypt the data key with any of the master keys:\n"
+	getDataKeyErr := getDataKeyError{
+		RequiredSuccessfulKeyGroups: m.ShamirThreshold,
+		GroupResults:                make([]error, len(m.KeyGroups)),
+	}
 	var parts [][]byte
-	for _, group := range m.KeyGroups {
-	keysLoop:
-		for _, key := range group {
-			svcKey := keyservice.KeyFromMasterKey(key)
-			for _, svc := range svcs {
-				rsp, err := svc.Decrypt(
-					context.Background(),
-					&keyservice.DecryptRequest{
-						Ciphertext: key.EncryptedDataKey(),
-						Key:        &svcKey,
-					})
-				if err != nil {
-					errMsg += fmt.Sprintf("\t%s: %s", key.ToString(), err)
-					continue
-				}
-				parts = append(parts, rsp.Plaintext)
-				// All keys in a key group encrypt the same part, so as soon
-				// as we decrypt it successfully with one key, we need to
-				// proceed with the next group
-				break keysLoop
-			}
+	for i, group := range m.KeyGroups {
+		part, err := decryptKeyGroup(group, svcs)
+		if err == nil {
+			parts = append(parts, part)
 		}
+		getDataKeyErr.GroupResults[i] = err
 	}
 	var dataKey []byte
 	if len(m.KeyGroups) > 1 {
 		if len(parts) < m.ShamirThreshold {
-			return nil, fmt.Errorf("not enough parts to recover data key with Shamir: need %d, have %d", m.ShamirThreshold, len(parts))
+			return nil, &getDataKeyErr
 		}
 		var err error
 		dataKey, err = shamir.Combine(parts)
@@ -472,7 +459,7 @@ func (m Metadata) GetDataKeyWithKeyServices(svcs []keyservice.KeyServiceClient)
 		}
 	} else {
 		if len(parts) != 1 {
-			return nil, fmt.Errorf("%s", errMsg)
+			return nil, &getDataKeyErr
 		}
 		dataKey = parts[0]
 	}
@@ -481,6 +468,55 @@ func (m Metadata) GetDataKeyWithKeyServices(svcs []keyservice.KeyServiceClient)
 	return dataKey, nil
 }
 
+// decryptKeyGroup tries to decrypt the contents of the provided KeyGroup with
+// any of the MasterKeys in the KeyGroup with any of the provided key services,
+// returning as soon as one key service succeeds.
+func decryptKeyGroup(group KeyGroup, svcs []keyservice.KeyServiceClient) ([]byte, error) {
+	var keyErrs []error
+	for _, key := range group {
+		part, err := decryptKey(key, svcs)
+		if err != nil {
+			keyErrs = append(keyErrs, err)
+		} else {
+			return part, nil
+		}
+	}
+	return nil, decryptKeyErrors(keyErrs)
+}
+
+// decryptKey tries to decrypt the contents of the provided MasterKey with any
+// of the key services, returning as soon as one key service succeeds.
+func decryptKey(key keys.MasterKey, svcs []keyservice.KeyServiceClient) ([]byte, error) {
+	svcKey := keyservice.KeyFromMasterKey(key)
+	var part []byte = nil
+	decryptErr := decryptKeyError{
+		keyName: key.ToString(),
+	}
+	for _, svc := range svcs {
+		// All keys in a key group encrypt the same part, so as soon
+		// as we decrypt it successfully with one key, we need to
+		// proceed with the next group
+		var err error
+		if part == nil {
+			var rsp *keyservice.DecryptResponse
+			rsp, err = svc.Decrypt(
+				context.Background(),
+				&keyservice.DecryptRequest{
+					Ciphertext: key.EncryptedDataKey(),
+					Key:        &svcKey,
+				})
+			if err == nil {
+				part = rsp.Plaintext
+			}
+		}
+		decryptErr.errs = append(decryptErr.errs, err)
+	}
+	if part != nil {
+		return part, nil
+	}
+	return nil, &decryptErr
+}
+
 // GetDataKey retrieves the data key from the first MasterKey in the Metadata's KeySources that's able to return it,
 // using the local KeyService
 func (m Metadata) GetDataKey() ([]byte, error) {
diff --git a/usererrors.go b/usererrors.go
new file mode 100644
index 000000000..f0f10813f
--- /dev/null
+++ b/usererrors.go
@@ -0,0 +1,162 @@
+package sops
+
+import (
+	"fmt"
+	"io/ioutil"
+	"strings"
+
+	"github.com/fatih/color"
+	"github.com/goware/prefixer"
+	wordwrap "github.com/mitchellh/go-wordwrap"
+)
+
+// UserError is a well-formatted error for the purpose of being displayed to
+// the end user.
+type UserError interface {
+	error
+	UserError() string
+}
+
+var statusSuccess = color.New(color.FgGreen).Sprint("SUCCESS")
+var statusFailed = color.New(color.FgRed).Sprint("FAILED")
+
+type getDataKeyError struct {
+	RequiredSuccessfulKeyGroups int
+	GroupResults                []error
+}
+
+func (err *getDataKeyError) successfulKeyGroups() int {
+	n := 0
+	for _, r := range err.GroupResults {
+		if r == nil {
+			n++
+		}
+	}
+	return n
+}
+
+func (err *getDataKeyError) Error() string {
+	return fmt.Sprintf("Error getting data key: %d successful groups "+
+		"required, got %d", err.RequiredSuccessfulKeyGroups,
+		err.successfulKeyGroups())
+}
+
+func (err *getDataKeyError) UserError() string {
+	var groupErrs []string
+	for i, res := range err.GroupResults {
+		groupErr := decryptGroupError{
+			err:       res,
+			groupName: fmt.Sprintf("%d", i),
+		}
+		groupErrs = append(groupErrs, groupErr.UserError())
+	}
+	var trailer string
+	if err.RequiredSuccessfulKeyGroups == 0 {
+		trailer = "Recovery failed because no master key was able to decrypt " +
+			"the file. In order for SOPS to recover the file, at least one key " +
+			"has to be successful, but none were."
+	} else {
+		trailer = fmt.Sprintf("Recovery failed because the file was "+
+			"encrypted with a Shamir threshold of %d, but only %d part(s) "+
+			"were successfully recovered, one for each successful key group. "+
+			"In order for SOPS to recover the file, at least %d groups have "+
+			"to be successful. In order for a group to be successful, "+
+			"decryption has to succeed with any of the keys in that key group.",
+			err.RequiredSuccessfulKeyGroups, err.successfulKeyGroups(),
+			err.RequiredSuccessfulKeyGroups)
+	}
+	trailer = wordwrap.WrapString(trailer, 75)
+	return fmt.Sprintf("Failed to get the data key required to "+
+		"decrypt the SOPS file.\n\n%s\n\n%s",
+		strings.Join(groupErrs, "\n\n"), trailer)
+}
+
+type decryptGroupError struct {
+	groupName string
+	err       error
+}
+
+func (r *decryptGroupError) Error() string {
+	return fmt.Sprintf("could not decryt group %s: %s", r.groupName, r.err)
+}
+
+func (r *decryptGroupError) UserError() string {
+	var status string
+	if r.err == nil {
+		status = statusSuccess
+	} else {
+		status = statusFailed
+	}
+	header := fmt.Sprintf(`Group %s: %s`, r.groupName, status)
+	if r.err == nil {
+		return header
+	}
+	message := r.err.Error()
+	if userError, ok := r.err.(UserError); ok {
+		message = userError.UserError()
+	}
+	reader := prefixer.New(strings.NewReader(message), "  ")
+	errMsg, _ := ioutil.ReadAll(reader)
+	return fmt.Sprintf("%s\n%s", header, string(errMsg))
+}
+
+type decryptKeyErrors []error
+
+func (e decryptKeyErrors) Error() string {
+	return fmt.Sprintf("error decrypting key: %s", []error(e))
+}
+
+func (e decryptKeyErrors) UserError() string {
+	var errStrs []string
+	for _, err := range []error(e) {
+		if userErr, ok := err.(UserError); ok {
+			errStrs = append(errStrs, userErr.UserError())
+		} else {
+			errStrs = append(errStrs, err.Error())
+		}
+	}
+	return strings.Join(errStrs, "\n\n")
+}
+
+type decryptKeyError struct {
+	keyName string
+	errs    []error
+}
+
+func (e *decryptKeyError) isSuccessful() bool {
+	for _, err := range e.errs {
+		if err == nil {
+			return true
+		}
+	}
+	return false
+}
+
+func (e *decryptKeyError) Error() string {
+	return fmt.Sprintf("error decrypting key %s: %s", e.keyName, e.errs)
+}
+
+func (e *decryptKeyError) UserError() string {
+	var status string
+	if e.isSuccessful() {
+		status = statusSuccess
+	} else {
+		status = statusFailed
+	}
+	header := fmt.Sprintf("%s: %s", e.keyName, status)
+	if e.isSuccessful() {
+		return header
+	}
+	var errMessages []string
+	for _, err := range e.errs {
+		wrappedErr := wordwrap.WrapString(err.Error(), 60)
+		reader := prefixer.New(strings.NewReader(wrappedErr), "  | ")
+		errMsg, _ := ioutil.ReadAll(reader)
+		errMsg[0] = '-'
+		errMessages = append(errMessages, string(errMsg))
+	}
+	joinedMsgs := strings.Join(errMessages, "\n\n")
+	reader := prefixer.New(strings.NewReader(joinedMsgs), "  ")
+	errMsg, _ := ioutil.ReadAll(reader)
+	return fmt.Sprintf("%s\n%s", header, string(errMsg))
+}