diff --git a/Sources/tart/OCI/Manifest.swift b/Sources/tart/OCI/Manifest.swift
index 955a016e..53769b91 100644
--- a/Sources/tart/OCI/Manifest.swift
+++ b/Sources/tart/OCI/Manifest.swift
@@ -78,7 +78,7 @@ struct OCIManifestConfig: Codable, Equatable {
   var digest: String
 }
 
-struct OCIManifestLayer: Codable, Equatable {
+struct OCIManifestLayer: Codable, Equatable, Hashable {
   var mediaType: String
   var size: Int
   var digest: String
@@ -113,6 +113,14 @@ struct OCIManifestLayer: Codable, Equatable {
   func uncompressedContentDigest() -> String? {
     annotations?[uncompressedContentDigestAnnotation]
   }
+
+  static func == (lhs: Self, rhs: Self) -> Bool {
+    return lhs.digest == rhs.digest
+  }
+
+  func hash(into hasher: inout Hasher) {
+    hasher.combine(digest)
+  }
 }
 
 struct Descriptor: Equatable {
diff --git a/Sources/tart/VMDirectory+OCI.swift b/Sources/tart/VMDirectory+OCI.swift
index c09e0986..07c59225 100644
--- a/Sources/tart/VMDirectory+OCI.swift
+++ b/Sources/tart/VMDirectory+OCI.swift
@@ -79,6 +79,9 @@ extension VMDirectory {
       nvram.write(data)
     }
     try nvram.close()
+
+    // Serialize VM's manifest to enable better de-duplication on subsequent "tart pull"'s
+    try manifest.toJSON().write(to: manifestURL)
   }
 
   func pushToRegistry(registry: Registry, references: [String], chunkSizeMb: Int, diskFormat: String) async throws -> RemoteName {
diff --git a/Sources/tart/VMDirectory.swift b/Sources/tart/VMDirectory.swift
index 650d8d2a..ccd7e791 100644
--- a/Sources/tart/VMDirectory.swift
+++ b/Sources/tart/VMDirectory.swift
@@ -23,6 +23,9 @@ struct VMDirectory: Prunable {
   var stateURL: URL {
     baseURL.appendingPathComponent("state.vzvmsave")
   }
+  var manifestURL: URL {
+    baseURL.appendingPathComponent("manifest.json")
+  }
 
   var explicitlyPulledMark: URL {
     baseURL.appendingPathComponent(".explicitly-pulled")
diff --git a/Sources/tart/VMStorageOCI.swift b/Sources/tart/VMStorageOCI.swift
index 0212698d..6a920f78 100644
--- a/Sources/tart/VMStorageOCI.swift
+++ b/Sources/tart/VMStorageOCI.swift
@@ -197,14 +197,8 @@ class VMStorageOCI: PrunableStorage {
 
       try await withTaskCancellationHandler(operation: {
         try await retry(maxAttempts: 5, backoff: .exponentialWithFullJitter(baseDelay: .seconds(5), maxDelay: .seconds(60))) {
-          var localLayerCache: LocalLayerCache? = nil
-
-          if name.reference.type == .Tag,
-             let vmDir = try? open(name),
-             let digest = try? digest(name),
-             let (manifest, _) = try? await registry.pullManifest(reference: digest) {
-            localLayerCache = try LocalLayerCache(vmDir.diskURL, manifest)
-          }
+          // Choose the best base image which has the most deduplication ratio
+          let localLayerCache = try await chooseLocalLayerCache(name, manifest, registry)
 
           try await tmpVMDir.pullFromRegistry(registry: registry, manifest: manifest, concurrency: concurrency, localLayerCache: localLayerCache)
         } recoverFromFailure: { error in
@@ -249,6 +243,57 @@ class VMStorageOCI: PrunableStorage {
 
     try gc()
   }
+
+  func chooseLocalLayerCache(_ name: RemoteName, _ manifest: OCIManifest, _ registry: Registry) async throws -> LocalLayerCache? {
+    // Establish a closure that will calculate how much bytes
+    // we'll de-duplicate if we re-use the given manifest
+    let target = Swift.Set(manifest.layers)
+
+    let calculateDeduplicatedBytes = { (manifest: OCIManifest) -> Int in
+      target.intersection(manifest.layers).map({ $0.size }).reduce(0, +)
+    }
+
+    // Load OCI VM images and their manifests (if present)
+    var candidates: [(name: String, vmDir: VMDirectory, manifest: OCIManifest, deduplicatedBytes: Int)] = []
+
+    for (name, vmDir, isSymlink) in try list() {
+      if isSymlink {
+        continue
+      }
+
+      guard let manifestJSON = try? Data(contentsOf: vmDir.manifestURL) else {
+        continue
+      }
+
+      guard let manifest = try? OCIManifest(fromJSON: manifestJSON) else {
+        continue
+      }
+
+      candidates.append((name, vmDir, manifest, calculateDeduplicatedBytes(manifest)))
+    }
+
+    // Previously we haven't stored the OCI VM image manifests, but still fetched the VM image manifest if
+    // what the user was trying to pull was a tagged image, and we already had that image in the OCI VM cache
+    //
+    // Keep supporting this behavior for backwards comaptibility, but only communicate
+    // with the registry if we haven't already retrieved the manifest for that OCI VM image.
+    if name.reference.type == .Tag,
+       let vmDir = try? open(name),
+       let digest = try? digest(name),
+       try !candidates.contains(where: {try $0.manifest.digest() == digest}),
+       let (manifest, _) = try? await registry.pullManifest(reference: digest) {
+      candidates.append((name.description, vmDir, manifest, calculateDeduplicatedBytes(manifest)))
+    }
+
+    // Now, find the best match based on how many bytes we'll de-duplicate
+    let choosen = candidates.max { left, right in
+      return left.deduplicatedBytes < right.deduplicatedBytes
+    }
+
+    return try choosen.flatMap({ choosen in
+      try LocalLayerCache(choosen.vmDir.diskURL, choosen.manifest)
+    })
+  }
 }
 
 extension URL {