diff --git a/docs/content/en/schemas/v1beta10.json b/docs/content/en/schemas/v1beta10.json
index 572139fc19c..9b9bdb18d29 100755
--- a/docs/content/en/schemas/v1beta10.json
+++ b/docs/content/en/schemas/v1beta10.json
@@ -595,6 +595,11 @@
     },
     "CustomDependencies": {
       "properties": {
+        "dockerfile": {
+          "$ref": "#/definitions/DockerfileDependency",
+          "description": "should be set if the artifact is built from a Dockerfile, from which skaffold can determine dependencies.",
+          "x-intellij-html-description": "should be set if the artifact is built from a Dockerfile, from which skaffold can determine dependencies."
+        },
         "ignore": {
           "items": {
             "type": "string"
@@ -615,12 +620,13 @@
         }
       },
       "preferredOrder": [
+        "dockerfile",
         "paths",
         "ignore"
       ],
       "additionalProperties": false,
-      "description": "*alpha* used to specify dependencies for an artifact built by a custom build script.",
-      "x-intellij-html-description": "<em>alpha</em> used to specify dependencies for an artifact built by a custom build script."
+      "description": "*alpha* used to specify dependencies for an artifact built by a custom build script. Either `dockerfile` or `paths` should be specified for file watching to work as expected.",
+      "x-intellij-html-description": "<em>alpha</em> used to specify dependencies for an artifact built by a custom build script. Either <code>dockerfile</code> or <code>paths</code> should be specified for file watching to work as expected."
     },
     "DateTimeTagger": {
       "properties": {
@@ -767,6 +773,40 @@
       "description": "contains information about the docker `config.json` to mount.",
       "x-intellij-html-description": "contains information about the docker <code>config.json</code> to mount."
     },
+    "DockerfileDependency": {
+      "properties": {
+        "buildArgs": {
+          "additionalProperties": {
+            "type": "string"
+          },
+          "type": "object",
+          "description": "arguments passed to the docker build. It also accepts environment variables via the go template syntax.",
+          "x-intellij-html-description": "arguments passed to the docker build. It also accepts environment variables via the go template syntax.",
+          "default": "{}",
+          "examples": [
+            "{\"key1\": \"value1\", \"key2\": \"value2\", \"key3\": \"{{.ENV_VARIABLE}}\"}"
+          ]
+        },
+        "path": {
+          "type": "string",
+          "description": "locates the Dockerfile relative to workspace.",
+          "x-intellij-html-description": "locates the Dockerfile relative to workspace."
+        },
+        "target": {
+          "type": "string",
+          "description": "Dockerfile target name to build.",
+          "x-intellij-html-description": "Dockerfile target name to build."
+        }
+      },
+      "preferredOrder": [
+        "path",
+        "target",
+        "buildArgs"
+      ],
+      "additionalProperties": false,
+      "description": "*alpha* used to specify a custom build artifact that is built from a Dockerfile. This allows skaffold to determine dependencies from the Dockerfile.",
+      "x-intellij-html-description": "<em>alpha</em> used to specify a custom build artifact that is built from a Dockerfile. This allows skaffold to determine dependencies from the Dockerfile."
+    },
     "EnvTemplateTagger": {
       "required": [
         "template"
diff --git a/pkg/skaffold/build/custom/dependencies.go b/pkg/skaffold/build/custom/dependencies.go
index 56fdf65e4c2..2143ae87724 100644
--- a/pkg/skaffold/build/custom/dependencies.go
+++ b/pkg/skaffold/build/custom/dependencies.go
@@ -26,15 +26,24 @@ import (
 )
 
 // GetDependencies returns dependencies listed for a custom artifact
-func GetDependencies(ctx context.Context, workspace string, a *latest.CustomArtifact) ([]string, error) {
-	files, err := docker.WalkWorkspace(workspace, a.Dependencies.Ignore, a.Dependencies.Paths)
-	if err != nil {
-		return nil, errors.Wrapf(err, "walking workspace %s", workspace)
-	}
-	var dependencies []string
-	for file := range files {
-		dependencies = append(dependencies, file)
+func GetDependencies(ctx context.Context, workspace string, a *latest.CustomArtifact, insecureRegistries map[string]bool) ([]string, error) {
+
+	switch {
+	case a.Dependencies.Dockerfile != nil:
+		dockerfile := a.Dependencies.Dockerfile
+		return docker.GetDependencies(ctx, workspace, dockerfile.Path, dockerfile.BuildArgs, insecureRegistries)
+
+	default:
+		files, err := docker.WalkWorkspace(workspace, a.Dependencies.Ignore, a.Dependencies.Paths)
+		if err != nil {
+			return nil, errors.Wrapf(err, "walking workspace %s", workspace)
+		}
+		var dependencies []string
+		for file := range files {
+			dependencies = append(dependencies, file)
+		}
+		sort.Strings(dependencies)
+		return dependencies, nil
 	}
-	sort.Strings(dependencies)
-	return dependencies, nil
+
 }
diff --git a/pkg/skaffold/build/custom/dependencies_test.go b/pkg/skaffold/build/custom/dependencies_test.go
index 35f0a4d0043..1fd2850f50c 100644
--- a/pkg/skaffold/build/custom/dependencies_test.go
+++ b/pkg/skaffold/build/custom/dependencies_test.go
@@ -25,7 +25,40 @@ import (
 	"github.com/GoogleContainerTools/skaffold/testutil"
 )
 
-func TestGetDependencies(t *testing.T) {
+func TestGetDependenciesDockerfile(t *testing.T) {
+	tmpDir, cleanup := testutil.NewTempDir(t)
+	defer cleanup()
+
+	// Directory structure:
+	//   foo
+	//   bar
+	// - baz
+	//     file
+	//   Dockerfile
+	tmpDir.Write("foo", "")
+	tmpDir.Write("bar", "")
+	tmpDir.Mkdir("baz")
+	tmpDir.Write("baz/file", "")
+	tmpDir.Write("Dockerfile", "FROM scratch \n ARG file \n COPY $file baz/file .")
+
+	customArtifact := &latest.CustomArtifact{
+		Dependencies: &latest.CustomDependencies{
+			Dockerfile: &latest.DockerfileDependency{
+				Path: "Dockerfile",
+				BuildArgs: map[string]*string{
+					"file": stringPointer("foo"),
+				},
+			},
+		},
+	}
+
+	expected := []string{"Dockerfile", "baz/file", "foo"}
+	deps, err := GetDependencies(context.Background(), tmpDir.Root(), customArtifact, nil)
+
+	testutil.CheckErrorAndDeepEqual(t, false, err, expected, deps)
+}
+
+func TestGetDependenciesPaths(t *testing.T) {
 	tmpDir, cleanup := testutil.NewTempDir(t)
 	defer cleanup()
 
@@ -66,9 +99,13 @@ func TestGetDependencies(t *testing.T) {
 					Paths:  test.paths,
 					Ignore: test.ignore,
 				},
-			})
+			}, nil)
 			testutil.CheckErrorAndDeepEqual(t, false, err, test.expected, deps)
 		})
 	}
 
 }
+
+func stringPointer(s string) *string {
+	return &s
+}
diff --git a/pkg/skaffold/build/local/local.go b/pkg/skaffold/build/local/local.go
index 7644f96749c..49aca07b5c6 100644
--- a/pkg/skaffold/build/local/local.go
+++ b/pkg/skaffold/build/local/local.go
@@ -124,7 +124,7 @@ func (b *Builder) DependenciesForArtifact(ctx context.Context, a *latest.Artifac
 		paths, err = jib.GetDependenciesGradle(ctx, a.Workspace, a.JibGradleArtifact)
 
 	case a.CustomArtifact != nil:
-		paths, err = custom.GetDependencies(ctx, a.Workspace, a.CustomArtifact)
+		paths, err = custom.GetDependencies(ctx, a.Workspace, a.CustomArtifact, b.insecureRegistries)
 
 	default:
 		return nil, fmt.Errorf("undefined artifact type: %+v", a.ArtifactType)
diff --git a/pkg/skaffold/schema/latest/config.go b/pkg/skaffold/schema/latest/config.go
index df7d6522a39..44649b8f365 100644
--- a/pkg/skaffold/schema/latest/config.go
+++ b/pkg/skaffold/schema/latest/config.go
@@ -566,7 +566,10 @@ type CustomArtifact struct {
 }
 
 // CustomDependencies *alpha* is used to specify dependencies for an artifact built by a custom build script.
+// Either `dockerfile` or `paths` should be specified for file watching to work as expected.
 type CustomDependencies struct {
+	// Dockerfile should be set if the artifact is built from a Dockerfile, from which skaffold can determine dependencies.
+	Dockerfile *DockerfileDependency `yaml:"dockerfile,omitempty" yamltags:"oneOf=dependency"`
 	// Paths should be set to the file dependencies for this artifact, so that the skaffold file watcher knows when to rebuild and perform file synchronization.
 	Paths []string `yaml:"paths,omitempty" yamltags:"oneOf=dependency"`
 	// Ignore specifies the paths that should be ignored by skaffold's file watcher. If a file exists in both `paths` and in `ignore`, it will be ignored, and will be excluded from both rebuilds and file synchronization.
@@ -574,6 +577,20 @@ type CustomDependencies struct {
 	Ignore []string `yaml:"ignore,omitempty"`
 }
 
+// DockerfileDependency *alpha* is used to specify a custom build artifact that is built from a Dockerfile. This allows skaffold to determine dependencies from the Dockerfile.
+type DockerfileDependency struct {
+	// Path locates the Dockerfile relative to workspace.
+	Path string `yaml:"path,omitempty"`
+
+	// Target is the Dockerfile target name to build.
+	Target string `yaml:"target,omitempty"`
+
+	// BuildArgs are arguments passed to the docker build.
+	// It also accepts environment variables via the go template syntax.
+	// For example: `{"key1": "value1", "key2": "value2", "key3": "{{.ENV_VARIABLE}}"}`.
+	BuildArgs map[string]*string `yaml:"buildArgs,omitempty"`
+}
+
 // KanikoArtifact *alpha* describes an artifact built from a Dockerfile,
 // with kaniko.
 type KanikoArtifact struct {