diff --git a/internal/tools/ooxmlgate.go b/internal/tools/ooxmlgate.go
index 292e995..5e647b5 100644
--- a/internal/tools/ooxmlgate.go
+++ b/internal/tools/ooxmlgate.go
@@ -14,14 +14,23 @@ import (
 	"encoding/xml"
 	"fmt"
 	"io"
+	"net/url"
 	"path"
 	"path/filepath"
 	"strings"
 )
 
 const (
+	nsPackageRel     = "http://schemas.openxmlformats.org/package/2006/relationships"
+	nsContentTypes   = "http://schemas.openxmlformats.org/package/2006/content-types"
 	nsPresentationML = "http://schemas.openxmlformats.org/presentationml/2006/main"
 	nsOfficeDocRel   = "http://schemas.openxmlformats.org/officeDocument/2006/relationships"
+	relOfficeDoc     = nsOfficeDocRel + "/officeDocument"
+	relStrictOffice  = "http://purl.oclc.org/ooxml/officeDocument/relationships/officeDocument"
+	ctWordDocument   = "application/vnd.openxmlformats-officedocument.wordprocessingml.document.main+xml"
+	ctWordTemplate   = "application/vnd.openxmlformats-officedocument.wordprocessingml.template.main+xml"
+	ctWordMacroDoc   = "application/vnd.ms-word.document.macroEnabled.main+xml"
+	ctWordMacroTpl   = "application/vnd.ms-word.template.macroEnabledTemplate.main+xml"
 	ctPresentation   = "application/vnd.openxmlformats-officedocument.presentationml.presentation.main+xml"
 	ctSlide          = "application/vnd.openxmlformats-officedocument.presentationml.slide+xml"
 	ctSlideLayout    = "application/vnd.openxmlformats-officedocument.presentationml.slideLayout+xml"
@@ -44,20 +53,324 @@ func ooxmlStructuralCheck(name string, content []byte) error {
 	}
 }
 
-// isWordprocessingMLPackage identifies Word OPC packages from their mandatory
-// main document part instead of trusting the caller-controlled filename. The
-// part is shared by document/template and macro-enabled variants.
+// isWordprocessingMLPackage identifies Word OPC packages from the package-level
+// officeDocument relationship and the resolved main part's content type. A
+// purported officeDocument package with malformed, ambiguous, or unsafe
+// metadata is treated as Word so the registration boundary fails closed.
 func isWordprocessingMLPackage(content []byte) bool {
 	zr, err := zip.NewReader(bytes.NewReader(content), int64(len(content)))
 	if err != nil {
 		return false
 	}
-	for _, file := range zr.File {
-		if strings.EqualFold(strings.TrimPrefix(file.Name, "/"), "word/document.xml") {
-			return true
+	isWord, purportsOfficeDocument, err := ooxmlClassifyWordPackage(zr)
+	if err != nil {
+		return purportsOfficeDocument
+	}
+	return isWord
+}
+
+func ooxmlClassifyWordPackage(zr *zip.Reader) (isWord, purportsOfficeDocument bool, err error) {
+	relsFile, found, err := ooxmlUniquePart(zr, "_rels/.rels")
+	if err != nil {
+		return false, true, err
+	}
+	if !found {
+		return false, false, nil
+	}
+	rels, purportsOfficeDocument, err := ooxmlPackageRelationships(relsFile)
+	if err != nil {
+		return false, purportsOfficeDocument, err
+	}
+
+	var officeRels []ooxmlRel
+	for _, rel := range rels {
+		if rel.typ == relOfficeDoc || rel.typ == relStrictOffice {
+			officeRels = append(officeRels, rel)
 		}
 	}
-	return false
+	if len(officeRels) == 0 {
+		return false, false, nil
+	}
+	if len(officeRels) != 1 {
+		return false, true, fmt.Errorf("package relationships contain %d officeDocument relationships", len(officeRels))
+	}
+
+	mainPart, err := ooxmlSafePackageTarget(officeRels[0].target, officeRels[0].targetMode)
+	if err != nil {
+		return false, true, err
+	}
+	if _, found, err := ooxmlUniquePartFold(zr, mainPart); err != nil || !found {
+		if err != nil {
+			return false, true, err
+		}
+		return false, true, fmt.Errorf("officeDocument target %q is missing", mainPart)
+	}
+
+	contentTypesFile, found, err := ooxmlUniquePart(zr, "[Content_Types].xml")
+	if err != nil {
+		return false, true, err
+	}
+	if !found {
+		return false, true, fmt.Errorf("officeDocument package is missing [Content_Types].xml")
+	}
+	contentTypes, err := ooxmlParseContentTypes(contentTypesFile)
+	if err != nil {
+		return false, true, err
+	}
+	contentType, found := contentTypes.contentType(mainPart)
+	if !found {
+		return false, true, fmt.Errorf("officeDocument target %q has no content type", mainPart)
+	}
+	return ooxmlIsWordMainContentType(contentType), true, nil
+}
+
+type ooxmlContentTypeTable struct {
+	defaults  map[string]string
+	overrides map[string]string
+}
+
+func (t ooxmlContentTypeTable) contentType(part string) (string, bool) {
+	if contentType, ok := t.overrides[strings.ToLower(part)]; ok {
+		return contentType, true
+	}
+	extension := strings.TrimPrefix(path.Ext(part), ".")
+	contentType, ok := t.defaults[strings.ToLower(extension)]
+	return contentType, ok
+}
+
+func ooxmlIsWordMainContentType(contentType string) bool {
+	switch contentType {
+	case ctWordDocument, ctWordTemplate, ctWordMacroDoc, ctWordMacroTpl:
+		return true
+	default:
+		return false
+	}
+}
+
+func ooxmlPackageRelationships(file *zip.File) ([]ooxmlRel, bool, error) {
+	rc, err := file.Open()
+	if err != nil {
+		return nil, false, fmt.Errorf("_rels/.rels cannot be read: %w", err)
+	}
+	defer rc.Close()
+
+	dec := xml.NewDecoder(rc)
+	var rels []ooxmlRel
+	seenIDs := map[string]bool{}
+	rootSeen := false
+	rootValid := false
+	depth := 0
+	purportsOfficeDocument := false
+	var metadataErr error
+	for {
+		tok, err := dec.Token()
+		if err == io.EOF {
+			break
+		}
+		if err != nil {
+			return nil, purportsOfficeDocument, fmt.Errorf("_rels/.rels is not valid XML: %w", err)
+		}
+		switch node := tok.(type) {
+		case xml.EndElement:
+			depth--
+			continue
+		case xml.StartElement:
+			depth++
+			if !rootSeen {
+				rootSeen = true
+				rootValid = node.Name.Space == nsPackageRel && node.Name.Local == "Relationships"
+				if !rootValid {
+					metadataErr = fmt.Errorf("_rels/.rels has an invalid Relationships root")
+				}
+				continue
+			}
+
+			var rel ooxmlRel
+			seenAttrs := map[string]bool{}
+			for _, attr := range node.Attr {
+				if attr.Name.Space != "" {
+					continue
+				}
+				if seenAttrs[attr.Name.Local] {
+					metadataErr = fmt.Errorf("_rels/.rels contains duplicate %s attributes", attr.Name.Local)
+				}
+				seenAttrs[attr.Name.Local] = true
+				switch attr.Name.Local {
+				case "Id":
+					rel.id = attr.Value
+				case "Type":
+					rel.typ = attr.Value
+				case "Target":
+					rel.target = attr.Value
+				case "TargetMode":
+					rel.targetMode = attr.Value
+				}
+			}
+			if rel.typ == relOfficeDoc || rel.typ == relStrictOffice {
+				purportsOfficeDocument = true
+			}
+			if depth != 2 || node.Name.Space != nsPackageRel || node.Name.Local != "Relationship" {
+				metadataErr = fmt.Errorf("_rels/.rels contains an invalid relationship element")
+				continue
+			}
+			if rel.id == "" || rel.typ == "" || rel.target == "" {
+				metadataErr = fmt.Errorf("_rels/.rels contains an incomplete Relationship")
+				continue
+			}
+			if seenIDs[rel.id] {
+				metadataErr = fmt.Errorf("_rels/.rels contains duplicate relationship Id %q", rel.id)
+				continue
+			}
+			seenIDs[rel.id] = true
+			rels = append(rels, rel)
+		}
+	}
+	if !rootSeen {
+		return nil, false, fmt.Errorf("_rels/.rels is empty")
+	}
+	if !rootValid || metadataErr != nil {
+		return nil, purportsOfficeDocument, metadataErr
+	}
+	return rels, purportsOfficeDocument, nil
+}
+
+func ooxmlParseContentTypes(file *zip.File) (ooxmlContentTypeTable, error) {
+	table := ooxmlContentTypeTable{
+		defaults:  map[string]string{},
+		overrides: map[string]string{},
+	}
+	rc, err := file.Open()
+	if err != nil {
+		return table, fmt.Errorf("[Content_Types].xml cannot be read: %w", err)
+	}
+	defer rc.Close()
+
+	dec := xml.NewDecoder(rc)
+	rootSeen := false
+	for {
+		tok, err := dec.Token()
+		if err == io.EOF {
+			break
+		}
+		if err != nil {
+			return table, fmt.Errorf("[Content_Types].xml is not valid XML: %w", err)
+		}
+		se, ok := tok.(xml.StartElement)
+		if !ok {
+			continue
+		}
+		if !rootSeen {
+			rootSeen = true
+			if se.Name.Space != nsContentTypes || se.Name.Local != "Types" {
+				return table, fmt.Errorf("[Content_Types].xml has an invalid Types root")
+			}
+			continue
+		}
+		if se.Name.Space != nsContentTypes {
+			continue
+		}
+		attrs := map[string]string{}
+		for _, attr := range se.Attr {
+			if attr.Name.Space == "" {
+				attrs[attr.Name.Local] = attr.Value
+			}
+		}
+		switch se.Name.Local {
+		case "Default":
+			extension := strings.ToLower(attrs["Extension"])
+			contentType := attrs["ContentType"]
+			if extension == "" || strings.ContainsAny(extension, ".\\/ \t\r\n") || contentType == "" {
+				return table, fmt.Errorf("[Content_Types].xml contains an invalid Default")
+			}
+			if _, exists := table.defaults[extension]; exists {
+				return table, fmt.Errorf("[Content_Types].xml contains duplicate Default for %q", extension)
+			}
+			table.defaults[extension] = contentType
+		case "Override":
+			partName, err := ooxmlSafePartName(attrs["PartName"])
+			if err != nil || attrs["ContentType"] == "" {
+				return table, fmt.Errorf("[Content_Types].xml contains an invalid Override")
+			}
+			key := strings.ToLower(partName)
+			if _, exists := table.overrides[key]; exists {
+				return table, fmt.Errorf("[Content_Types].xml contains duplicate Override for %q", partName)
+			}
+			table.overrides[key] = attrs["ContentType"]
+		}
+	}
+	if !rootSeen {
+		return table, fmt.Errorf("[Content_Types].xml is empty")
+	}
+	return table, nil
+}
+
+func ooxmlSafePackageTarget(target, targetMode string) (string, error) {
+	if targetMode != "" && !strings.EqualFold(targetMode, "Internal") {
+		return "", fmt.Errorf("officeDocument target must be internal")
+	}
+	return ooxmlSafePartPath(target, strings.HasPrefix(target, "/"))
+}
+
+func ooxmlSafePartName(partName string) (string, error) {
+	if !strings.HasPrefix(partName, "/") {
+		return "", fmt.Errorf("OPC part name must be absolute")
+	}
+	return ooxmlSafePartPath(partName, true)
+}
+
+func ooxmlSafePartPath(raw string, absolute bool) (string, error) {
+	if raw == "" || strings.ContainsAny(raw, "\\\x00") {
+		return "", fmt.Errorf("unsafe OPC part path %q", raw)
+	}
+	parsed, err := url.Parse(raw)
+	if err != nil || parsed.IsAbs() || parsed.Host != "" || parsed.Opaque != "" || parsed.RawQuery != "" || parsed.Fragment != "" {
+		return "", fmt.Errorf("unsafe OPC part path %q", raw)
+	}
+	decoded, err := url.PathUnescape(parsed.EscapedPath())
+	if err != nil || strings.ContainsAny(decoded, "\\\x00") {
+		return "", fmt.Errorf("unsafe OPC part path %q", raw)
+	}
+	if absolute != strings.HasPrefix(decoded, "/") {
+		return "", fmt.Errorf("unsafe OPC part path %q", raw)
+	}
+	decoded = strings.TrimPrefix(decoded, "/")
+	if decoded == "" || strings.HasSuffix(decoded, "/") {
+		return "", fmt.Errorf("unsafe OPC part path %q", raw)
+	}
+	for _, segment := range strings.Split(decoded, "/") {
+		if segment == "" || segment == "." || segment == ".." {
+			return "", fmt.Errorf("unsafe OPC part path %q", raw)
+		}
+	}
+	return decoded, nil
+}
+
+func ooxmlUniquePart(zr *zip.Reader, name string) (*zip.File, bool, error) {
+	var found *zip.File
+	for _, file := range zr.File {
+		if file.Name != name {
+			continue
+		}
+		if found != nil {
+			return nil, false, fmt.Errorf("duplicate OPC metadata part %s", name)
+		}
+		found = file
+	}
+	return found, found != nil, nil
+}
+
+func ooxmlUniquePartFold(zr *zip.Reader, name string) (*zip.File, bool, error) {
+	var found *zip.File
+	for _, file := range zr.File {
+		if !strings.EqualFold(file.Name, name) {
+			continue
+		}
+		if found != nil {
+			return nil, false, fmt.Errorf("duplicate OPC part %s", name)
+		}
+		found = file
+	}
+	return found, found != nil, nil
 }
 
 // ooxmlCheckParts 校验容器与必备正文部件存在、XML 合法、命名空间前缀齐备
@@ -538,9 +851,10 @@ func ooxmlPart(zr *zip.Reader, name string) (*zip.File, error) {
 
 // ooxmlRel 是 rels 部件里的一条关系：Id、类型 URI 与目标（原样保留相对形式）。
 type ooxmlRel struct {
-	id     string
-	typ    string
-	target string
+	id         string
+	typ        string
+	target     string
+	targetMode string
 }
 
 // ooxmlRels 解析 part 的关系表（<dir>/_rels/<base>.rels）。
diff --git a/internal/tools/ooxmlgate_test.go b/internal/tools/ooxmlgate_test.go
index b858435..227775b 100644
--- a/internal/tools/ooxmlgate_test.go
+++ b/internal/tools/ooxmlgate_test.go
@@ -31,18 +31,47 @@ func zipOf(t *testing.T, files map[string]string) []byte {
 }
 
 const (
-	gateCTXML  = `<?xml version="1.0"?><Types xmlns="http://schemas.openxmlformats.org/package/2006/content-types"><Default Extension="xml" ContentType="application/xml"/><Default Extension="rels" ContentType="application/vnd.openxmlformats-package.relationships+xml"/></Types>`
-	gateSlide  = `<?xml version="1.0"?><p:sld xmlns:p="http://schemas.openxmlformats.org/presentationml/2006/main"><p:cSld><p:spTree/></p:cSld></p:sld>`
-	gateLayout = `<?xml version="1.0"?><p:sldLayout xmlns:p="http://schemas.openxmlformats.org/presentationml/2006/main"><p:cSld><p:spTree/></p:cSld></p:sldLayout>`
-	gateMaster = `<?xml version="1.0"?><p:sldMaster xmlns:p="http://schemas.openxmlformats.org/presentationml/2006/main" xmlns:r="http://schemas.openxmlformats.org/officeDocument/2006/relationships"><p:cSld><p:spTree/></p:cSld><p:sldLayoutIdLst><p:sldLayoutId id="2147483647" r:id="rId1"/></p:sldLayoutIdLst></p:sldMaster>`
-	gateTheme  = `<?xml version="1.0"?><a:theme xmlns:a="http://schemas.openxmlformats.org/drawingml/2006/main"/>`
+	gatePackageRelNS = "http://schemas.openxmlformats.org/package/2006/relationships"
+	gateOfficeRel    = "http://schemas.openxmlformats.org/officeDocument/2006/relationships/officeDocument"
+	gateStrictOffice = "http://purl.oclc.org/ooxml/officeDocument/relationships/officeDocument"
+	gateContentNS    = "http://schemas.openxmlformats.org/package/2006/content-types"
+	gateCTXML        = `<?xml version="1.0"?><Types xmlns="http://schemas.openxmlformats.org/package/2006/content-types"><Default Extension="xml" ContentType="application/xml"/><Default Extension="rels" ContentType="application/vnd.openxmlformats-package.relationships+xml"/></Types>`
+	gateSlide        = `<?xml version="1.0"?><p:sld xmlns:p="http://schemas.openxmlformats.org/presentationml/2006/main"><p:cSld><p:spTree/></p:cSld></p:sld>`
+	gateLayout       = `<?xml version="1.0"?><p:sldLayout xmlns:p="http://schemas.openxmlformats.org/presentationml/2006/main"><p:cSld><p:spTree/></p:cSld></p:sldLayout>`
+	gateMaster       = `<?xml version="1.0"?><p:sldMaster xmlns:p="http://schemas.openxmlformats.org/presentationml/2006/main" xmlns:r="http://schemas.openxmlformats.org/officeDocument/2006/relationships"><p:cSld><p:spTree/></p:cSld><p:sldLayoutIdLst><p:sldLayoutId id="2147483647" r:id="rId1"/></p:sldLayoutIdLst></p:sldMaster>`
+	gateTheme        = `<?xml version="1.0"?><a:theme xmlns:a="http://schemas.openxmlformats.org/drawingml/2006/main"/>`
 )
 
 func relXML(rels ...string) string {
-	return `<?xml version="1.0"?><Relationships xmlns="http://schemas.openxmlformats.org/package/2006/relationships">` +
+	return `<?xml version="1.0"?><Relationships xmlns="` + gatePackageRelNS + `">` +
 		strings.Join(rels, "") + `</Relationships>`
 }
 
+func gateOfficePackage(t *testing.T, rels, contentTypes, mainPart string) []byte {
+	t.Helper()
+	files := map[string]string{
+		"_rels/.rels":         rels,
+		"[Content_Types].xml": contentTypes,
+	}
+	if mainPart != "" {
+		files[strings.TrimPrefix(mainPart, "/")] = `<?xml version="1.0"?><root/>`
+	}
+	return zipOf(t, files)
+}
+
+func gateOfficeRelXML(relType, target, targetMode string) string {
+	mode := ""
+	if targetMode != "" {
+		mode = ` TargetMode="` + targetMode + `"`
+	}
+	return relXML(`<Relationship Id="rId1" Type="` + relType + `" Target="` + target + `"` + mode + `/>`)
+}
+
+func gateOverrideCT(part, contentType string) string {
+	return `<?xml version="1.0"?><Types xmlns="` + gateContentNS + `"><Override PartName="/` +
+		strings.TrimPrefix(part, "/") + `" ContentType="` + contentType + `"/></Types>`
+}
+
 const (
 	relSlide    = `<Relationship Id="rId1" Type="http://schemas.openxmlformats.org/officeDocument/2006/relationships/slide" Target="slides/slide1.xml"/>`
 	relMaster   = `<Relationship Id="rId2" Type="http://schemas.openxmlformats.org/officeDocument/2006/relationships/slideMaster" Target="slideMasters/slideMaster1.xml"/>`
@@ -365,20 +394,22 @@ func TestRegisterArtifactRejectsRenamedWordprocessingMLPackages(t *testing.T) {
 
 	wordTypes := []struct {
 		name        string
+		mainPart    string
+		relType     string
 		contentType string
 	}{
-		{"report.zip", "application/vnd.openxmlformats-officedocument.wordprocessingml.document.main+xml"},
-		{"macro.bin", "application/vnd.ms-word.document.macroEnabled.main+xml"},
-		{"template.data", "application/vnd.openxmlformats-officedocument.wordprocessingml.template.main+xml"},
-		{"template.docx ", "application/vnd.ms-word.template.macroEnabledTemplate.main+xml"},
+		{"report.zip", "custom/main.xml", gateOfficeRel, "application/vnd.openxmlformats-officedocument.wordprocessingml.document.main+xml"},
+		{"macro.bin", "word/document.xml", gateOfficeRel, "application/vnd.ms-word.document.macroEnabled.main+xml"},
+		{"template.data", "templates/body.xml", gateStrictOffice, "application/vnd.openxmlformats-officedocument.wordprocessingml.template.main+xml"},
+		{"macro-template.payload", "package/document.xml", gateOfficeRel, "application/vnd.ms-word.template.macroEnabledTemplate.main+xml"},
 	}
 	for _, test := range wordTypes {
 		t.Run(test.name, func(t *testing.T) {
-			contentTypes := `<?xml version="1.0"?><Types xmlns="http://schemas.openxmlformats.org/package/2006/content-types"><Override PartName="/word/document.xml" ContentType="` + test.contentType + `"/></Types>`
-			pkg := zipOf(t, map[string]string{
-				"[Content_Types].xml": contentTypes,
-				"word/document.xml":   `<?xml version="1.0"?><w:document xmlns:w="http://schemas.openxmlformats.org/wordprocessingml/2006/main"/>`,
-			})
+			pkg := gateOfficePackage(t,
+				gateOfficeRelXML(test.relType, test.mainPart, ""),
+				gateOverrideCT(test.mainPart, test.contentType),
+				test.mainPart,
+			)
 			if err := os.WriteFile(filepath.Join(sandbox, test.name), pkg, 0o644); err != nil {
 				t.Fatal(err)
 			}
@@ -389,9 +420,41 @@ func TestRegisterArtifactRejectsRenamedWordprocessingMLPackages(t *testing.T) {
 		})
 	}
 
+	defaultTyped := gateOfficePackage(t,
+		gateOfficeRelXML(gateOfficeRel, "alternate/main.wml", ""),
+		`<?xml version="1.0"?><Types xmlns="`+gateContentNS+`"><Default Extension="wml" ContentType="application/vnd.openxmlformats-officedocument.wordprocessingml.document.main+xml"/></Types>`,
+		"alternate/main.wml",
+	)
+	if err := os.WriteFile(filepath.Join(sandbox, "default-typed.pkg"), defaultTyped, 0o644); err != nil {
+		t.Fatal(err)
+	}
+	res := interpCall(t, r, rc, "register_artifact", `{"path":"default-typed.pkg"}`)
+	if res.Status != "error" || !strings.Contains(res.Output, "direct Word registration is forbidden") {
+		t.Fatalf("default-typed WordprocessingML package must be refused: %s %s", res.Status, res.Output)
+	}
+
+	fakeWordPart := zipOf(t, map[string]string{
+		"word/document.xml": `<?xml version="1.0"?><not-word/>`,
+		"data/payload.json": `{"ok":true}`,
+	})
+	if err := os.WriteFile(filepath.Join(sandbox, "same-name.zip"), fakeWordPart, 0o644); err != nil {
+		t.Fatal(err)
+	}
+	res = interpCall(t, r, rc, "register_artifact", `{"path":"same-name.zip"}`)
+	if res.Status != "ok" || !strings.Contains(res.Output, "已登记交付物") {
+		t.Fatalf("ordinary ZIP with a same-name part must register: %s %s", res.Status, res.Output)
+	}
+
+	spreadsheet := gateOfficePackage(t,
+		gateOfficeRelXML(gateOfficeRel, "xl/workbook.xml", ""),
+		gateOverrideCT("xl/workbook.xml", "application/vnd.openxmlformats-officedocument.spreadsheetml.sheet.main+xml"),
+		"xl/workbook.xml",
+	)
+
 	allowed := map[string][]byte{
-		"dataset.zip": zipOf(t, map[string]string{"data/payload.json": `{"ok":true}`}),
-		"payload.bin": {0x00, 0x01, 0x02, 0xff},
+		"dataset.zip":     zipOf(t, map[string]string{"data/payload.json": `{"ok":true}`}),
+		"spreadsheet.pkg": spreadsheet,
+		"payload.bin":     {0x00, 0x01, 0x02, 0xff},
 	}
 	for name, content := range allowed {
 		if err := os.WriteFile(filepath.Join(sandbox, name), content, 0o644); err != nil {
@@ -404,6 +467,81 @@ func TestRegisterArtifactRejectsRenamedWordprocessingMLPackages(t *testing.T) {
 	}
 }
 
+func TestRegisterArtifactRejectsMalformedAmbiguousOrUnsafeOfficeDocumentMetadata(t *testing.T) {
+	r := NewRegistry()
+	if err := RegisterExecTools(r); err != nil {
+		t.Fatal(err)
+	}
+	root := t.TempDir()
+	rc := &execFake{root: root, owner: "o1", conv: "c1", execOn: true}
+	sandbox := filepath.Join(root, "o1", "c1")
+	if err := os.MkdirAll(sandbox, 0o755); err != nil {
+		t.Fatal(err)
+	}
+
+	const wordType = "application/vnd.openxmlformats-officedocument.wordprocessingml.document.main+xml"
+	validCT := gateOverrideCT("custom/main.xml", wordType)
+	validRel := gateOfficeRelXML(gateOfficeRel, "custom/main.xml", "")
+	tests := []struct {
+		name         string
+		rels         string
+		contentTypes string
+	}{
+		{
+			name:         "malformed-relationships.pkg",
+			rels:         `<?xml version="1.0"?><Relationships xmlns="` + gatePackageRelNS + `"><Relationship Id="rId1" Type="` + gateOfficeRel + `" Target="custom/main.xml">`,
+			contentTypes: validCT,
+		},
+		{
+			name: "duplicate-office-relationships.pkg",
+			rels: relXML(
+				`<Relationship Id="rId1" Type="`+gateOfficeRel+`" Target="custom/main.xml"/>`,
+				`<Relationship Id="rId2" Type="`+gateOfficeRel+`" Target="other/main.xml"/>`,
+			),
+			contentTypes: validCT,
+		},
+		{
+			name:         "malformed-content-types.pkg",
+			rels:         validRel,
+			contentTypes: `<?xml version="1.0"?><Types xmlns="` + gateContentNS + `"><Override PartName="/custom/main.xml" ContentType="` + wordType + `">`,
+		},
+		{
+			name: "duplicate-content-type.pkg",
+			rels: validRel,
+			contentTypes: `<?xml version="1.0"?><Types xmlns="` + gateContentNS + `">` +
+				`<Override PartName="/custom/main.xml" ContentType="` + wordType + `"/>` +
+				`<Override PartName="/custom/main.xml" ContentType="application/xml"/></Types>`,
+		},
+		{
+			name:         "missing-main-content-type.pkg",
+			rels:         validRel,
+			contentTypes: `<?xml version="1.0"?><Types xmlns="` + gateContentNS + `"></Types>`,
+		},
+		{
+			name:         "traversal-target.pkg",
+			rels:         gateOfficeRelXML(gateOfficeRel, "../custom/main.xml", ""),
+			contentTypes: validCT,
+		},
+		{
+			name:         "external-target.pkg",
+			rels:         gateOfficeRelXML(gateOfficeRel, "https://example.invalid/main.xml", "External"),
+			contentTypes: validCT,
+		},
+	}
+	for _, test := range tests {
+		t.Run(test.name, func(t *testing.T) {
+			pkg := gateOfficePackage(t, test.rels, test.contentTypes, "custom/main.xml")
+			if err := os.WriteFile(filepath.Join(sandbox, test.name), pkg, 0o644); err != nil {
+				t.Fatal(err)
+			}
+			res := interpCall(t, r, rc, "register_artifact", `{"path":`+mustJSON(t, test.name)+`}`)
+			if res.Status != "error" || !strings.Contains(res.Output, "direct Word registration is forbidden") {
+				t.Fatalf("unsafe officeDocument metadata must fail closed: %s %s", res.Status, res.Output)
+			}
+		})
+	}
+}
+
 func mustJSON(t *testing.T, value string) string {
 	t.Helper()
 	raw, err := json.Marshal(value)