diff --git a/post-processor/hcp-vagrant-registry/post-processor.go b/post-processor/hcp-vagrant-registry/post-processor.go
index e3511b92..14f1ff06 100644
--- a/post-processor/hcp-vagrant-registry/post-processor.go
+++ b/post-processor/hcp-vagrant-registry/post-processor.go
@@ -15,6 +15,7 @@ import (
 	"io"
 	"log"
 	"os"
+	"path"
 	"strings"
 
 	"github.com/hashicorp/hcl/v2/hcldec"
@@ -410,7 +411,7 @@ func metadataFromVagrantBox(boxfile string) (metadata map[string]interface{}, er
 			return nil, fmt.Errorf("Failed reading header info from box tar archive: %w", err)
 		}
 
-		if hdr.Name == "metadata.json" {
+		if path.Base(hdr.Name) == "metadata.json" {
 			var contents []byte
 			contents, err = io.ReadAll(tr)
 			if err != nil {
diff --git a/post-processor/hcp-vagrant-registry/post-processor_test.go b/post-processor/hcp-vagrant-registry/post-processor_test.go
index c46c83af..cdf8c98f 100644
--- a/post-processor/hcp-vagrant-registry/post-processor_test.go
+++ b/post-processor/hcp-vagrant-registry/post-processor_test.go
@@ -912,6 +912,64 @@ func TestPostProcessor(t *testing.T) {
 					c["no_direct_upload"] = false
 				},
 			},
+			{
+				desc: "OK - archive paths are relative",
+				stack: []stubResponse{
+					{
+						Method:     "POST",
+						Path:       "/oauth2/token",
+						Response:   `{"access_token": "TEST_TOKEN", "expiry": 0}`,
+						StatusCode: 200,
+					},
+					{
+						Method:     "GET",
+						Path:       "/vagrant/2022-09-30/registry/hashicorp/box/precise64",
+						Response:   `{}`,
+						StatusCode: 200,
+					},
+					{
+						Method:     "GET",
+						Path:       "/vagrant/2022-09-30/registry/hashicorp/box/precise64/version/0.5",
+						Response:   `{"version": {"state": "UNRELEASED"}}`,
+						StatusCode: 200,
+					},
+					{
+						Method:     "GET",
+						Path:       "/vagrant/2022-09-30/registry/hashicorp/box/precise64/version/0.5/provider/virtualbox",
+						Response:   `{}`,
+						StatusCode: 200,
+					},
+					{
+						Method:     "GET",
+						Path:       "/vagrant/2022-09-30/registry/hashicorp/box/precise64/version/0.5/provider/virtualbox/architecture/amd64",
+						Response:   `{}`,
+						StatusCode: 200,
+					},
+					{
+						Method:     "PUT",
+						Path:       "/vagrant/2022-09-30/registry/hashicorp/box/precise64/version/0.5/provider/virtualbox/architecture/amd64",
+						Response:   `{}`,
+						StatusCode: 200,
+					},
+					{
+						Method:     "GET",
+						Path:       "/vagrant/2022-09-30/registry/hashicorp/box/precise64/version/0.5/provider/virtualbox/architecture/amd64/upload",
+						Response:   fmt.Sprintf(`{"url": "%s"}`, uploadURL),
+						StatusCode: 200,
+					},
+					{
+						Method:     "PUT",
+						Path:       "/vagrant/2022-09-30/registry/hashicorp/box/precise64/version/0.5/release",
+						Response:   `{}`,
+						StatusCode: 200,
+					},
+				},
+				files: tarFiles{
+					{"./foo.txt", "This is a foo file"},
+					{"./bar.txt", "This is a bar file"},
+					{"./metadata.json", `{"provider": "virtualbox", "architecture": "amd64"}`},
+				},
+			},
 		}
 
 		for _, tc := range testCases {