diff --git a/cli/command/context/create.go b/cli/command/context/create.go
index 1c93a1881a..e4a5258bfa 100644
--- a/cli/command/context/create.go
+++ b/cli/command/context/create.go
@@ -24,6 +24,10 @@ type CreateOptions struct {
 	Description string
 	Docker      map[string]string
 	From        string
+
+	// Additional Metadata to store in the context. This option is not
+	// currently exposed to the user.
+	metaData map[string]any
 }
 
 func longCreateDescription() string {
@@ -94,7 +98,8 @@ func createNewContext(contextStore store.ReaderWriter, o *CreateOptions) error {
 			docker.DockerEndpoint: dockerEP,
 		},
 		Metadata: command.DockerContext{
-			Description: o.Description,
+			Description:      o.Description,
+			AdditionalFields: o.metaData,
 		},
 		Name: o.Name,
 	}
diff --git a/cli/command/context/export-import_test.go b/cli/command/context/export-import_test.go
index fc3952c300..9aabd6ab44 100644
--- a/cli/command/context/export-import_test.go
+++ b/cli/command/context/export-import_test.go
@@ -8,14 +8,18 @@ import (
 	"path/filepath"
 	"testing"
 
+	"github.com/docker/cli/cli/command"
 	"github.com/docker/cli/cli/streams"
 	"gotest.tools/v3/assert"
+	is "gotest.tools/v3/assert/cmp"
 )
 
 func TestExportImportWithFile(t *testing.T) {
 	contextFile := filepath.Join(t.TempDir(), "exported")
 	cli := makeFakeCli(t)
-	createTestContext(t, cli, "test")
+	createTestContext(t, cli, "test", map[string]any{
+		"MyCustomMetadata": t.Name(),
+	})
 	cli.ErrBuffer().Reset()
 	assert.NilError(t, RunExport(cli, &ExportOptions{
 		ContextName: "test",
@@ -29,18 +33,26 @@ func TestExportImportWithFile(t *testing.T) {
 	assert.NilError(t, err)
 	context2, err := cli.ContextStore().GetMetadata("test2")
 	assert.NilError(t, err)
-	assert.DeepEqual(t, context1.Endpoints, context2.Endpoints)
-	assert.DeepEqual(t, context1.Metadata, context2.Metadata)
-	assert.Equal(t, "test", context1.Name)
-	assert.Equal(t, "test2", context2.Name)
 
-	assert.Equal(t, "test2\n", cli.OutBuffer().String())
-	assert.Equal(t, "Successfully imported context \"test2\"\n", cli.ErrBuffer().String())
+	assert.Check(t, is.DeepEqual(context1.Metadata, command.DockerContext{
+		Description:      "description of test",
+		AdditionalFields: map[string]any{"MyCustomMetadata": t.Name()},
+	}))
+
+	assert.Check(t, is.DeepEqual(context1.Endpoints, context2.Endpoints))
+	assert.Check(t, is.DeepEqual(context1.Metadata, context2.Metadata))
+	assert.Check(t, is.Equal("test", context1.Name))
+	assert.Check(t, is.Equal("test2", context2.Name))
+
+	assert.Check(t, is.Equal("test2\n", cli.OutBuffer().String()))
+	assert.Check(t, is.Equal("Successfully imported context \"test2\"\n", cli.ErrBuffer().String()))
 }
 
 func TestExportImportPipe(t *testing.T) {
 	cli := makeFakeCli(t)
-	createTestContext(t, cli, "test")
+	createTestContext(t, cli, "test", map[string]any{
+		"MyCustomMetadata": t.Name(),
+	})
 	cli.ErrBuffer().Reset()
 	cli.OutBuffer().Reset()
 	assert.NilError(t, RunExport(cli, &ExportOptions{
@@ -56,13 +68,19 @@ func TestExportImportPipe(t *testing.T) {
 	assert.NilError(t, err)
 	context2, err := cli.ContextStore().GetMetadata("test2")
 	assert.NilError(t, err)
-	assert.DeepEqual(t, context1.Endpoints, context2.Endpoints)
-	assert.DeepEqual(t, context1.Metadata, context2.Metadata)
-	assert.Equal(t, "test", context1.Name)
-	assert.Equal(t, "test2", context2.Name)
 
-	assert.Equal(t, "test2\n", cli.OutBuffer().String())
-	assert.Equal(t, "Successfully imported context \"test2\"\n", cli.ErrBuffer().String())
+	assert.Check(t, is.DeepEqual(context1.Metadata, command.DockerContext{
+		Description:      "description of test",
+		AdditionalFields: map[string]any{"MyCustomMetadata": t.Name()},
+	}))
+
+	assert.Check(t, is.DeepEqual(context1.Endpoints, context2.Endpoints))
+	assert.Check(t, is.DeepEqual(context1.Metadata, context2.Metadata))
+	assert.Check(t, is.Equal("test", context1.Name))
+	assert.Check(t, is.Equal("test2", context2.Name))
+
+	assert.Check(t, is.Equal("test2\n", cli.OutBuffer().String()))
+	assert.Check(t, is.Equal("Successfully imported context \"test2\"\n", cli.ErrBuffer().String()))
 }
 
 func TestExportExistingFile(t *testing.T) {
diff --git a/cli/command/context/inspect_test.go b/cli/command/context/inspect_test.go
index 703898ed53..68ce35ffb0 100644
--- a/cli/command/context/inspect_test.go
+++ b/cli/command/context/inspect_test.go
@@ -10,7 +10,9 @@ import (
 
 func TestInspect(t *testing.T) {
 	cli := makeFakeCli(t)
-	createTestContext(t, cli, "current")
+	createTestContext(t, cli, "current", map[string]any{
+		"MyCustomMetadata": "MyCustomMetadataValue",
+	})
 	cli.OutBuffer().Reset()
 	assert.NilError(t, runInspect(cli, inspectOptions{
 		refs: []string{"current"},
diff --git a/cli/command/context/list_test.go b/cli/command/context/list_test.go
index 1b264a6e85..9370bf6d2d 100644
--- a/cli/command/context/list_test.go
+++ b/cli/command/context/list_test.go
@@ -11,17 +11,19 @@ import (
 func createTestContexts(t *testing.T, cli command.Cli, name ...string) {
 	t.Helper()
 	for _, n := range name {
-		createTestContext(t, cli, n)
+		createTestContext(t, cli, n, nil)
 	}
 }
 
-func createTestContext(t *testing.T, cli command.Cli, name string) {
+func createTestContext(t *testing.T, cli command.Cli, name string, metaData map[string]any) {
 	t.Helper()
 
 	err := RunCreate(cli, &CreateOptions{
 		Name:        name,
 		Description: "description of " + name,
 		Docker:      map[string]string{keyHost: "https://someswarmserver.example.com"},
+
+		metaData: metaData,
 	})
 	assert.NilError(t, err)
 }
diff --git a/cli/command/context/remove_test.go b/cli/command/context/remove_test.go
index f42c4fe7eb..ab2f8ba216 100644
--- a/cli/command/context/remove_test.go
+++ b/cli/command/context/remove_test.go
@@ -57,7 +57,7 @@ func TestRemoveCurrentForce(t *testing.T) {
 
 func TestRemoveDefault(t *testing.T) {
 	cli := makeFakeCli(t)
-	createTestContext(t, cli, "other")
+	createTestContext(t, cli, "other", nil)
 	cli.SetCurrentContext("current")
 	err := RunRemove(cli, RemoveOptions{}, []string{"default"})
 	assert.ErrorContains(t, err, `default: context "default" cannot be removed`)
diff --git a/cli/command/context/show_test.go b/cli/command/context/show_test.go
index 40ac58ad05..eab0941692 100644
--- a/cli/command/context/show_test.go
+++ b/cli/command/context/show_test.go
@@ -8,7 +8,7 @@ import (
 
 func TestShow(t *testing.T) {
 	cli := makeFakeCli(t)
-	createTestContext(t, cli, "current")
+	createTestContext(t, cli, "current", nil)
 	cli.SetCurrentContext("current")
 
 	cli.OutBuffer().Reset()
diff --git a/cli/command/context/testdata/inspect.golden b/cli/command/context/testdata/inspect.golden
index ffc790180d..a023169d7a 100644
--- a/cli/command/context/testdata/inspect.golden
+++ b/cli/command/context/testdata/inspect.golden
@@ -2,7 +2,8 @@
     {
         "Name": "current",
         "Metadata": {
-            "Description": "description of current"
+            "Description": "description of current",
+            "MyCustomMetadata": "MyCustomMetadataValue"
         },
         "Endpoints": {
             "docker": {
diff --git a/cli/command/context/update_test.go b/cli/command/context/update_test.go
index 553f67fd1a..0e4a639145 100644
--- a/cli/command/context/update_test.go
+++ b/cli/command/context/update_test.go
@@ -34,7 +34,7 @@ func TestUpdateDescriptionOnly(t *testing.T) {
 
 func TestUpdateDockerOnly(t *testing.T) {
 	cli := makeFakeCli(t)
-	createTestContext(t, cli, "test")
+	createTestContext(t, cli, "test", nil)
 	assert.NilError(t, RunUpdate(cli, &UpdateOptions{
 		Name: "test",
 		Docker: map[string]string{