diff --git a/server/api/registry/timeline/[...pkg].get.ts b/server/api/registry/timeline/[...pkg].get.ts
index 948decc7bf..1c4be296cb 100644
--- a/server/api/registry/timeline/[...pkg].get.ts
+++ b/server/api/registry/timeline/[...pkg].get.ts
@@ -1,5 +1,5 @@
 import { normalizeLicense } from '#shared/utils/npm'
-import { hasBuiltInTypes } from '~~/shared/utils/package-analysis'
+import { analyzePackage, hasBuiltInTypes } from '~~/shared/utils/package-analysis'
 
 const DEFAULT_LIMIT = 25
 
@@ -82,9 +82,44 @@ export default defineCachedEventHandler(
           }
         })
         .sort((a, b) => Date.parse(b.time) - Date.parse(a.time))
+      const visibleVersions = allVersions.slice(offset, offset + limit)
+
+      // File-aware detection is limited to potential removal events: metadata-untyped
+      // versions with an older typed release. Checking every untyped version would
+      // require additional registry and file-tree requests.
+      const possibleTypeRemovals = visibleVersions
+        .filter(version => {
+          if (version.hasTypes) return false
+
+          const versionIndex = allVersions.indexOf(version)
+          return allVersions
+            .slice(versionIndex + 1)
+            .some(previousVersion => previousVersion.hasTypes)
+        })
+        .map(async version => {
+          try {
+            const { pkg, typesPackage, files } = await fetchPackageWithTypesAndFiles(
+              packageName,
+              version.version,
+            )
+
+            const analysis = analyzePackage(pkg, {
+              typesPackage,
+              files,
+            })
+
+            if (analysis.types.kind === 'included') {
+              version.hasTypes = true
+            }
+          } catch {
+            // Preserve the metadata-only result when the file list is unavailable.
+          }
+        })
+
+      await Promise.all(possibleTypeRemovals)
 
       return {
-        versions: allVersions.slice(offset, offset + limit),
+        versions: visibleVersions,
         total: allVersions.length,
       } satisfies TimelineResponse
     } catch (error: unknown) {
diff --git a/test/unit/server/api/registry/timeline/pkg.get.spec.ts b/test/unit/server/api/registry/timeline/pkg.get.spec.ts
index 44fea5a101..0d7cbf3acc 100644
--- a/test/unit/server/api/registry/timeline/pkg.get.spec.ts
+++ b/test/unit/server/api/registry/timeline/pkg.get.spec.ts
@@ -3,7 +3,9 @@ import { createError, type H3Event } from 'h3'
 import type { Packument, PackumentVersion } from '#shared/types/npm-registry'
 
 const fetchNpmPackageMock = vi.fn()
+const fetchPackageWithTypesAndFilesMock = vi.fn()
 vi.stubGlobal('fetchNpmPackage', fetchNpmPackageMock)
+vi.stubGlobal('fetchPackageWithTypesAndFiles', fetchPackageWithTypesAndFilesMock)
 vi.stubGlobal('defineCachedEventHandler', (fn: Function) => fn)
 vi.stubGlobal('CACHE_MAX_AGE_FIVE_MINUTES', 300)
 
@@ -228,6 +230,83 @@ describe('timeline API', () => {
     expect(result.versions[0]!.hasTypes).toBe(true)
   })
 
+  it('sets hasTypes for consecutive versions with declaration files', async () => {
+    routerParam = 'my-pkg'
+
+    fetchNpmPackageMock.mockResolvedValue(
+      makePackument({
+        versions: {
+          '1.0.0': {
+            types: './dist/index.d.ts',
+          },
+          '2.0.0': {
+            main: './dist/index.mjs',
+          },
+          '3.0.0': {
+            main: './dist/index.mjs',
+          },
+        },
+        time: {
+          '1.0.0': '2024-01-01T00:00:00Z',
+          '2.0.0': '2025-01-01T00:00:00Z',
+          '3.0.0': '2026-01-01T00:00:00Z',
+        },
+      }),
+    )
+
+    fetchPackageWithTypesAndFilesMock.mockImplementation(
+      async (packageName: string, version: string) => ({
+        pkg: {
+          name: packageName,
+          version,
+          main: './dist/index.mjs',
+        },
+        files: new Set(['dist/index.mjs', 'dist/index.d.mts']),
+      }),
+    )
+
+    const result = await handler(fakeEvent)
+
+    expect(fetchPackageWithTypesAndFilesMock).toHaveBeenCalledWith('my-pkg', '2.0.0')
+    expect(fetchPackageWithTypesAndFilesMock).toHaveBeenCalledWith('my-pkg', '3.0.0')
+    expect(result.versions).toHaveLength(3)
+    expect(result.versions[0]?.hasTypes).toBe(true)
+    expect(result.versions[1]?.hasTypes).toBe(true)
+    expect(result.versions[2]?.hasTypes).toBe(true)
+  })
+
+  it('keeps hasTypes unset when declarations are removed', async () => {
+    routerParam = 'my-pkg'
+
+    fetchNpmPackageMock.mockResolvedValue(
+      makePackument({
+        versions: {
+          '1.0.0': { types: './dist/index.d.ts' },
+          '2.0.0': { main: './dist/index.mjs' },
+        },
+        time: {
+          '1.0.0': '2024-01-01T00:00:00Z',
+          '2.0.0': '2025-01-01T00:00:00Z',
+        },
+      }),
+    )
+
+    fetchPackageWithTypesAndFilesMock.mockResolvedValue({
+      pkg: {
+        name: 'my-pkg',
+        version: '2.0.0',
+        main: './dist/index.mjs',
+      },
+      files: new Set(['dist/index.mjs']),
+    })
+
+    const result = await handler(fakeEvent)
+
+    expect(result.versions).toHaveLength(2)
+    expect(result.versions[0]?.hasTypes).toBeUndefined()
+    expect(result.versions[1]?.hasTypes).toBe(true)
+  })
+
   it('sets hasTrustedPublisher when trustedPublisher is true', async () => {
     routerParam = 'my-pkg'