diff --git a/pkg/skaffold/build/cache/lookup.go b/pkg/skaffold/build/cache/lookup.go
index c7544853841..5af76ae654c 100644
--- a/pkg/skaffold/build/cache/lookup.go
+++ b/pkg/skaffold/build/cache/lookup.go
@@ -75,22 +75,35 @@ func (c *cache) lookup(ctx context.Context, a *latest.Artifact, tag string, plat
 	pls := platforms.GetPlatforms(a.ImageName)
 	// TODO (gaghosh): allow `tryImport` when the Docker daemon starts supporting multiarch images
 	// See https://github.com/docker/buildx/issues/1220#issuecomment-1189996403
-	if !cacheHit && !pls.IsMultiPlatform() {
-		var pl v1.Platform
-		if len(pls.Platforms) == 1 {
-			pl = util.ConvertToV1Platform(pls.Platforms[0])
-		}
-		if entry, err = c.tryImport(ctx, a, tag, hash, pl); err != nil {
-			log.Entry(ctx).Debugf("Could not import artifact from Docker, building instead (%s)", err)
-			return needsBuilding{hash: hash}
-		}
-	}
 
 	if isLocal, err := c.isLocalImage(a.ImageName); err != nil {
 		return failed{err}
 	} else if isLocal {
+		if !cacheHit && !pls.IsMultiPlatform() {
+			var pl v1.Platform
+			if len(pls.Platforms) == 1 {
+				pl = util.ConvertToV1Platform(pls.Platforms[0])
+			}
+			if entry, err = c.tryImport(ctx, a, tag, hash, pl); err != nil {
+				log.Entry(ctx).Debugf("Could not import artifact from Docker, building instead (%s)", err)
+				return needsBuilding{hash: hash}
+			}
+		}
 		return c.lookupLocal(ctx, hash, tag, entry)
 	}
+	if !cacheHit {
+		entry := ImageDetails{}
+		if digest, err := docker.RemoteDigest(tag, c.cfg, nil); err == nil {
+			log.Entry(ctx).Debugf("Added digest for %s to cache entry", tag)
+			entry.Digest = digest
+			entry.ID = ""
+		}
+		log.Entry(ctx).Debugf("remote digest Error %s", err)
+
+		c.cacheMutex.Lock()
+		c.artifactCache[hash] = entry
+		c.cacheMutex.Unlock()
+	}
 	return c.lookupRemote(ctx, hash, tag, pls.Platforms, entry)
 }
 
@@ -120,8 +133,10 @@ func (c *cache) lookupLocal(ctx context.Context, hash, tag string, entry ImageDe
 }
 
 func (c *cache) lookupRemote(ctx context.Context, hash, tag string, platforms []specs.Platform, entry ImageDetails) cacheDetails {
+	log.Entry(ctx).Debugf("Looking up %s tag when in entry it's %s", tag, entry.Digest)
 	if remoteDigest, err := docker.RemoteDigest(tag, c.cfg, nil); err == nil {
 		// Image exists remotely with the same tag and digest
+		log.Entry(ctx).Debugf("Found %s remote", tag)
 		if remoteDigest == entry.Digest {
 			return found{hash: hash}
 		}
@@ -129,7 +144,9 @@ func (c *cache) lookupRemote(ctx context.Context, hash, tag string, platforms []
 
 	// Image exists remotely with a different tag
 	fqn := tag + "@" + entry.Digest // Actual tag will be ignored but we need the registry and the digest part of it.
+	log.Entry(ctx).Debugf("Looking up %s tag with the full fqn %s", tag, entry.Digest)
 	if remoteDigest, err := docker.RemoteDigest(fqn, c.cfg, nil); err == nil {
+		log.Entry(ctx).Debugf("Found %s with the full fqn", tag)
 		if remoteDigest == entry.Digest {
 			return needsRemoteTagging{hash: hash, tag: tag, digest: entry.Digest, platforms: platforms}
 		}
diff --git a/pkg/skaffold/build/cache/retrieve_test.go b/pkg/skaffold/build/cache/retrieve_test.go
index b66b9783aab..703f1162967 100644
--- a/pkg/skaffold/build/cache/retrieve_test.go
+++ b/pkg/skaffold/build/cache/retrieve_test.go
@@ -222,7 +222,11 @@ func TestCacheBuildRemote(t *testing.T) {
 		})
 
 		// Mock Docker
-		dockerDaemon := fakeLocalDaemon(&testutil.FakeAPIClient{})
+		api := &testutil.FakeAPIClient{}
+		api = api.Add("artifact1:tag1", "sha256:51ae7fa00c92525c319404a3a6d400e52ff9372c5a39cb415e0486fe425f3165")
+		api = api.Add("artifact2:tag2", "sha256:35bdf2619f59e6f2372a92cb5486f4a0bf9b86e0e89ee0672864db6ed9c51539")
+
+		dockerDaemon := fakeLocalDaemon(api)
 		t.Override(&docker.NewAPIClient, func(context.Context, docker.Config) (docker.LocalDaemon, error) {
 			return dockerDaemon, nil
 		})
@@ -310,7 +314,11 @@ func TestCacheFindMissing(t *testing.T) {
 		})
 
 		// Mock Docker
-		dockerDaemon := fakeLocalDaemon(&testutil.FakeAPIClient{})
+		api := &testutil.FakeAPIClient{}
+		api = api.Add("artifact1:tag1", "sha256:51ae7fa00c92525c319404a3a6d400e52ff9372c5a39cb415e0486fe425f3165")
+		api = api.Add("artifact2:tag2", "sha256:35bdf2619f59e6f2372a92cb5486f4a0bf9b86e0e89ee0672864db6ed9c51539")
+
+		dockerDaemon := fakeLocalDaemon(api)
 		t.Override(&docker.NewAPIClient, func(context.Context, docker.Config) (docker.LocalDaemon, error) {
 			return dockerDaemon, nil
 		})
@@ -339,7 +347,7 @@ func TestCacheFindMissing(t *testing.T) {
 			pipeline:  latest.Pipeline{Build: latest.BuildConfig{BuildType: latest.BuildType{LocalBuild: &latest.LocalBuild{TryImportMissing: true}}}},
 			cacheFile: tmpDir.Path("cache"),
 		}
-		artifactCache, err := NewCache(context.Background(), cfg, func(imageName string) (bool, error) { return false, nil }, deps, graph.ToArtifactGraph(artifacts), make(mockArtifactStore))
+		artifactCache, err := NewCache(context.Background(), cfg, func(imageName string) (bool, error) { return true, nil }, deps, graph.ToArtifactGraph(artifacts), make(mockArtifactStore))
 		t.CheckNoError(err)
 
 		// Because the artifacts are in the docker registry, we expect them to be imported correctly.
diff --git a/pkg/skaffold/runner/new.go b/pkg/skaffold/runner/new.go
index 4adc8518f97..747fdf0ffca 100644
--- a/pkg/skaffold/runner/new.go
+++ b/pkg/skaffold/runner/new.go
@@ -229,14 +229,17 @@ func setupTrigger(triggerName string, setIntent func(bool), setAutoTrigger func(
 func isImageLocal(runCtx *runcontext.RunContext, imageName string) (bool, error) {
 	pipeline, found := runCtx.PipelineForImage(imageName)
 	if !found {
+		log.Entry(context.TODO()).Debugf("Didn't find pipeline for image %s. Using default pipeline!", imageName)
 		pipeline = runCtx.DefaultPipeline()
 	}
 	if pipeline.Build.GoogleCloudBuild != nil || pipeline.Build.Cluster != nil {
+		log.Entry(context.TODO()).Debugf("Image %s is remote because it has GoogleCloudBuild or pipeline.Build.Cluster", imageName)
 		return false, nil
 	}
 
 	// if we're deploying to local Docker, all images must be local
 	if pipeline.Deploy.DockerDeploy != nil {
+		log.Entry(context.TODO()).Debugf("Image %s is local because it has docker deploy", imageName)
 		return true, nil
 	}