diff --git a/indexer/controller/coalesce.go b/indexer/controller/coalesce.go
index d7c1e0afc..95af0fc41 100644
--- a/indexer/controller/coalesce.go
+++ b/indexer/controller/coalesce.go
@@ -128,7 +128,7 @@ func MergeSR(source *claircore.IndexReport, merge []*claircore.IndexReport) *cla
 		}
 
 		for k, v := range ir.Files {
-			source.Files[k] = v
+			source.Files[k] = append(source.Files[k], v...)
 		}
 	}
 	return source
diff --git a/indexer/controller/controller.go b/indexer/controller/controller.go
index a39103582..a37b6b51e 100644
--- a/indexer/controller/controller.go
+++ b/indexer/controller/controller.go
@@ -41,7 +41,7 @@ func New(options *indexer.Options) *Controller {
 		Environments:  map[string][]*claircore.Environment{},
 		Distributions: map[string]*claircore.Distribution{},
 		Repositories:  map[string]*claircore.Repository{},
-		Files:         map[string]claircore.File{},
+		Files:         map[string][]claircore.File{},
 	}
 
 	s := &Controller{
diff --git a/indexreport.go b/indexreport.go
index cf3e8ba37..4e7628e3c 100644
--- a/indexreport.go
+++ b/indexreport.go
@@ -34,7 +34,7 @@ type IndexReport struct {
 	// an error string in the case the index did not succeed
 	Err string `json:"err"`
 	// Files doesn't end up in the json report but needs to be available at post-coalesce
-	Files map[string]File `json:"-"`
+	Files map[string][]File `json:"-"`
 }
 
 // IndexRecords returns a list of IndexRecords derived from the IndexReport
diff --git a/whiteout/coalescer.go b/whiteout/coalescer.go
index 0e7a3cac0..4e2c5fba5 100644
--- a/whiteout/coalescer.go
+++ b/whiteout/coalescer.go
@@ -14,9 +14,9 @@ func (c *coalescer) Coalesce(ctx context.Context, layerArtifacts []*indexer.Laye
 	for _, l := range layerArtifacts {
 		for _, f := range l.Files {
 			if ir.Files == nil {
-				ir.Files = make(map[string]claircore.File)
+				ir.Files = make(map[string][]claircore.File)
 			}
-			ir.Files[l.Hash.String()] = f
+			ir.Files[l.Hash.String()] = append(ir.Files[l.Hash.String()], f)
 		}
 	}
 	return ir, nil
diff --git a/whiteout/resolver.go b/whiteout/resolver.go
index d98cac5f1..e05f42ea0 100644
--- a/whiteout/resolver.go
+++ b/whiteout/resolver.go
@@ -32,19 +32,21 @@ func (r *Resolver) Resolve(ctx context.Context, ir *claircore.IndexReport, layer
 				packageLayer = ir.Environments[pkgID][i].IntroducedIn.String()
 			}
 		}
-		for fileLayer, f := range ir.Files {
-			// Check if it's a whiteout file, if it applies to the package's
-			// filepath and if the layer the whiteout file came from came after.
-			// The spec states: "Whiteout files MUST only apply to resources in
-			// lower/parent layers" hence why we don't check if they're in the same
-			// layer.
-			if f.Kind == claircore.FileKindWhiteout && ls.isChildOf(fileLayer, packageLayer) && fileIsDeleted(pkg.Filepath, f.Path) {
-				packageDeleted = true
-				zlog.Debug(ctx).
-					Str("package name", pkg.Name).
-					Str("package file", pkg.Filepath).
-					Str("whiteout file", f.Path).
-					Msg("package determined to be deleted")
+		for fileLayer, fs := range ir.Files {
+			for _, f := range fs {
+				// Check if it's a whiteout file, if it applies to the package's
+				// filepath and if the layer the whiteout file came from came after.
+				// The spec states: "Whiteout files MUST only apply to resources in
+				// lower/parent layers" hence why we don't check if they're in the same
+				// layer.
+				if f.Kind == claircore.FileKindWhiteout && ls.isChildOf(fileLayer, packageLayer) && fileIsDeleted(pkg.Filepath, f.Path) {
+					packageDeleted = true
+					zlog.Debug(ctx).
+						Str("package name", pkg.Name).
+						Str("package file", pkg.Filepath).
+						Str("whiteout file", f.Path).
+						Msg("package determined to be deleted")
+				}
 			}
 		}
 		if !packageDeleted {
diff --git a/whiteout/resolver_test.go b/whiteout/resolver_test.go
index 0212435ad..342a5f9c3 100644
--- a/whiteout/resolver_test.go
+++ b/whiteout/resolver_test.go
@@ -51,10 +51,12 @@ func TestResolver(t *testing.T) {
 					"1": {{IntroducedIn: firstLayerHash}},
 					"2": {{IntroducedIn: firstLayerHash}},
 				},
-				Files: map[string]claircore.File{
+				Files: map[string][]claircore.File{
 					secondLayerHash.String(): {
-						Path: "a/path/to/some/file/site-packages/.wh.a_package",
-						Kind: claircore.FileKindWhiteout,
+						{
+							Path: "a/path/to/some/file/site-packages/.wh.a_package",
+							Kind: claircore.FileKindWhiteout,
+						},
 					},
 				},
 			},
@@ -82,18 +84,20 @@ func TestResolver(t *testing.T) {
 					"1": {{IntroducedIn: firstLayerHash}},
 					"2": {{IntroducedIn: firstLayerHash}},
 				},
-				Files: map[string]claircore.File{
+				Files: map[string][]claircore.File{
 					secondLayerHash.String(): {
-						Path: "a/path/to/some/different_file/site-packages/.wh.a_package",
-						Kind: claircore.FileKindWhiteout,
-					},
-					secondLayerHash.String(): {
-						Path: "a/path/to/some/different_file/.wh.site-packages",
-						Kind: claircore.FileKindWhiteout,
-					},
-					secondLayerHash.String(): {
-						Path: "a/path/to/some/.wh.different_file",
-						Kind: claircore.FileKindWhiteout,
+						{
+							Path: "a/path/to/some/different_file/site-packages/.wh.a_package",
+							Kind: claircore.FileKindWhiteout,
+						},
+						{
+							Path: "a/path/to/some/different_file/.wh.site-packages",
+							Kind: claircore.FileKindWhiteout,
+						},
+						{
+							Path: "a/path/to/some/.wh.different_file",
+							Kind: claircore.FileKindWhiteout,
+						},
 					},
 				},
 			},
@@ -121,10 +125,12 @@ func TestResolver(t *testing.T) {
 					"1": {{IntroducedIn: firstLayerHash}},
 					"2": {{IntroducedIn: firstLayerHash}},
 				},
-				Files: map[string]claircore.File{
+				Files: map[string][]claircore.File{
 					secondLayerHash.String(): {
-						Path: "a/path/to/some/file/.wh.site-packages",
-						Kind: claircore.FileKindWhiteout,
+						{
+							Path: "a/path/to/some/file/.wh.site-packages",
+							Kind: claircore.FileKindWhiteout,
+						},
 					},
 				},
 			},
@@ -152,10 +158,12 @@ func TestResolver(t *testing.T) {
 					"1": {{IntroducedIn: firstLayerHash}},
 					"2": {{IntroducedIn: firstLayerHash}},
 				},
-				Files: map[string]claircore.File{
-					firstLayerHash.String(): { // whiteout is in the same layer as packages
-						Path: "a/path/to/some/file/site-packages/.wh.b_package",
-						Kind: claircore.FileKindWhiteout,
+				Files: map[string][]claircore.File{
+					firstLayerHash.String(): {
+						{ // whiteout is in the same layer as packages
+							Path: "a/path/to/some/file/site-packages/.wh.b_package",
+							Kind: claircore.FileKindWhiteout,
+						},
 					},
 				},
 			},
@@ -183,10 +191,12 @@ func TestResolver(t *testing.T) {
 					"1": {{IntroducedIn: firstLayerHash}},
 					"2": {{IntroducedIn: firstLayerHash}},
 				},
-				Files: map[string]claircore.File{
+				Files: map[string][]claircore.File{
 					secondLayerHash.String(): {
-						Path: "a/path/to/some/file/site/.wh..wh..opq",
-						Kind: claircore.FileKindWhiteout,
+						{
+							Path: "a/path/to/some/file/site/.wh..wh..opq",
+							Kind: claircore.FileKindWhiteout,
+						},
 					},
 				},
 			},
@@ -214,10 +224,12 @@ func TestResolver(t *testing.T) {
 					"1": {{IntroducedIn: firstLayerHash}},
 					"2": {{IntroducedIn: firstLayerHash}},
 				},
-				Files: map[string]claircore.File{
+				Files: map[string][]claircore.File{
 					secondLayerHash.String(): {
-						Path: "a/path/to/some/file/site-packages/.wh..wh..opq",
-						Kind: claircore.FileKindWhiteout,
+						{
+							Path: "a/path/to/some/file/site-packages/.wh..wh..opq",
+							Kind: claircore.FileKindWhiteout,
+						},
 					},
 				},
 			},
@@ -240,10 +252,12 @@ func TestResolver(t *testing.T) {
 				Environments: map[string][]*claircore.Environment{
 					"1": {{IntroducedIn: firstLayerHash}, {IntroducedIn: thirdLayerHash}},
 				},
-				Files: map[string]claircore.File{
-					secondLayerHash.String(): { // whiteout is sandwiched
-						Path: "a/path/to/some/file/site-packages/.wh.a_package",
-						Kind: claircore.FileKindWhiteout,
+				Files: map[string][]claircore.File{
+					secondLayerHash.String(): {
+						{ // whiteout is sandwiched
+							Path: "a/path/to/some/file/site-packages/.wh.a_package",
+							Kind: claircore.FileKindWhiteout,
+						},
 					},
 				},
 			},