diff --git a/cli/command/trust/common.go b/cli/command/trust/common.go
index 751259d5cb..4cc876a121 100644
--- a/cli/command/trust/common.go
+++ b/cli/command/trust/common.go
@@ -14,6 +14,7 @@ import (
 	"github.com/theupdateframework/notary"
 	"github.com/theupdateframework/notary/client"
 	"github.com/theupdateframework/notary/tuf/data"
+	"vbom.ml/util/sortorder"
 )
 
 // trustTagKey represents a unique signed tag and hex-encoded hash pair
@@ -149,7 +150,7 @@ func matchReleasedSignatures(allTargets []client.TargetSignedStruct) []trustTagR
 		signatureRows = append(signatureRows, trustTagRow{targetKey, signers})
 	}
 	sort.Slice(signatureRows, func(i, j int) bool {
-		return signatureRows[i].SignedTag < signatureRows[j].SignedTag
+		return sortorder.NaturalLess(signatureRows[i].SignedTag, signatureRows[j].SignedTag)
 	})
 	return signatureRows
 }
diff --git a/cli/command/trust/common_test.go b/cli/command/trust/common_test.go
new file mode 100644
index 0000000000..279e7fa79c
--- /dev/null
+++ b/cli/command/trust/common_test.go
@@ -0,0 +1,33 @@
+package trust
+
+import (
+	"testing"
+
+	"github.com/docker/cli/cli/trust"
+	"github.com/theupdateframework/notary/client"
+	"github.com/theupdateframework/notary/tuf/data"
+	"gotest.tools/assert"
+	is "gotest.tools/assert/cmp"
+)
+
+func TestMatchReleasedSignaturesSortOrder(t *testing.T) {
+	var releasesRole = data.DelegationRole{BaseRole: data.BaseRole{Name: trust.ReleasesRole}}
+	targets := []client.TargetSignedStruct{
+		{Target: client.Target{Name: "target10-foo"}, Role: releasesRole},
+		{Target: client.Target{Name: "target1-foo"}, Role: releasesRole},
+		{Target: client.Target{Name: "target2-foo"}, Role: releasesRole},
+	}
+
+	rows := matchReleasedSignatures(targets)
+
+	var targetNames []string
+	for _, r := range rows {
+		targetNames = append(targetNames, r.SignedTag)
+	}
+	expected := []string{
+		"target1-foo",
+		"target2-foo",
+		"target10-foo",
+	}
+	assert.Check(t, is.DeepEqual(expected, targetNames))
+}
diff --git a/cli/command/trust/inspect_pretty.go b/cli/command/trust/inspect_pretty.go
index f9104ce2c0..24c811b904 100644
--- a/cli/command/trust/inspect_pretty.go
+++ b/cli/command/trust/inspect_pretty.go
@@ -8,6 +8,7 @@ import (
 	"github.com/docker/cli/cli/command"
 	"github.com/docker/cli/cli/command/formatter"
 	"github.com/theupdateframework/notary/client"
+	"vbom.ml/util/sortorder"
 )
 
 func prettyPrintTrustInfo(cli command.Cli, remote string) error {
@@ -86,7 +87,7 @@ func printSignerInfo(out io.Writer, roleToKeyIDs map[string][]string) error {
 		})
 	}
 	sort.Slice(formattedSignerInfo, func(i, j int) bool {
-		return formattedSignerInfo[i].Name < formattedSignerInfo[j].Name
+		return sortorder.NaturalLess(formattedSignerInfo[i].Name, formattedSignerInfo[j].Name)
 	})
 	return formatter.SignerInfoWrite(signerInfoCtx, formattedSignerInfo)
 }
diff --git a/cli/command/trust/inspect_pretty_test.go b/cli/command/trust/inspect_pretty_test.go
index 8c5141b331..703dac02d0 100644
--- a/cli/command/trust/inspect_pretty_test.go
+++ b/cli/command/trust/inspect_pretty_test.go
@@ -1,6 +1,7 @@
 package trust
 
 import (
+	"bytes"
 	"encoding/hex"
 	"io/ioutil"
 	"testing"
@@ -440,3 +441,20 @@ func TestFormatAdminRole(t *testing.T) {
 	targetsRoleWithSigs := client.RoleWithSignatures{Role: targetsRole, Signatures: nil}
 	assert.Check(t, is.Equal("Repository Key:\tabc, key11, key99\n", formatAdminRole(targetsRoleWithSigs)))
 }
+
+func TestPrintSignerInfoSortOrder(t *testing.T) {
+	roleToKeyIDs := map[string][]string{
+		"signer2-foo":  {"B"},
+		"signer10-foo": {"C"},
+		"signer1-foo":  {"A"},
+	}
+
+	expected := `SIGNER              KEYS
+signer1-foo         A
+signer2-foo         B
+signer10-foo        C
+`
+	buf := new(bytes.Buffer)
+	assert.NilError(t, printSignerInfo(buf, roleToKeyIDs))
+	assert.Check(t, is.Equal(expected, buf.String()))
+}