diff --git a/CHANGELOG.md b/CHANGELOG.md
index 9be6fb29..c599fc88 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -4,6 +4,8 @@
 
 - Fixed panic bug when assigning a global variable
   ([#229](https://github.com/go-task/task/issues/229), [#243](https://github.com/go-task/task/issues/234)).
+- A task with `method: checksum` will now re-run if generated files are deleted
+  ([#228](https://github.com/go-task/task/pull/228), [#238](https://github.com/go-task/task/issues/238)).
 
 ## v2.6.0 - 2019-07-21
 
diff --git a/internal/status/checksum.go b/internal/status/checksum.go
index 44331047..572d4650 100644
--- a/internal/status/checksum.go
+++ b/internal/status/checksum.go
@@ -14,10 +14,11 @@ import (
 // Checksum validades if a task is up to date by calculating its source
 // files checksum
 type Checksum struct {
-	Dir     string
-	Task    string
-	Sources []string
-	Dry     bool
+	Dir       string
+	Task      string
+	Sources   []string
+	Generates []string
+	Dry       bool
 }
 
 // IsUpToDate implements the Checker interface
@@ -27,7 +28,7 @@ func (c *Checksum) IsUpToDate() (bool, error) {
 	data, _ := ioutil.ReadFile(checksumFile)
 	oldMd5 := strings.TrimSpace(string(data))
 
-	sources, err := glob(c.Dir, c.Sources)
+	sources, err := globs(c.Dir, c.Sources)
 	if err != nil {
 		return false, err
 	}
@@ -43,6 +44,23 @@ func (c *Checksum) IsUpToDate() (bool, error) {
 			return false, err
 		}
 	}
+
+	if len(c.Generates) > 0 {
+		// For each specified 'generates' field, check whether the files actually exist
+		for _, g := range c.Generates {
+			generates, err := glob(c.Dir, g)
+			if os.IsNotExist(err) {
+				return false, nil
+			}
+			if err != nil {
+				return false, err
+			}
+			if len(generates) == 0 {
+				return false, nil
+			}
+		}
+	}
+
 	return oldMd5 == newMd5, nil
 }
 
@@ -50,21 +68,14 @@ func (c *Checksum) checksum(files ...string) (string, error) {
 	h := md5.New()
 
 	for _, f := range files {
+		// also sum the filename, so checksum changes for renaming a file
+		if _, err := io.Copy(h, strings.NewReader(filepath.Base(f))); err != nil {
+			return "", err
+		}
 		f, err := os.Open(f)
 		if err != nil {
 			return "", err
 		}
-		info, err := f.Stat()
-		if err != nil {
-			return "", err
-		}
-		if info.IsDir() {
-			continue
-		}
-		// also sum the filename, so checksum changes for renaming a file
-		if _, err = io.Copy(h, strings.NewReader(info.Name())); err != nil {
-			return "", err
-		}
 		if _, err = io.Copy(h, f); err != nil {
 			return "", err
 		}
diff --git a/internal/status/glob.go b/internal/status/glob.go
index 305e0f9b..a70f663d 100644
--- a/internal/status/glob.go
+++ b/internal/status/glob.go
@@ -1,6 +1,7 @@
 package status
 
 import (
+	"os"
 	"path/filepath"
 	"sort"
 
@@ -9,21 +10,41 @@ import (
 	"github.com/mattn/go-zglob"
 )
 
-func glob(dir string, globs []string) (files []string, err error) {
+func globs(dir string, globs []string) ([]string, error) {
+	files := make([]string, 0)
 	for _, g := range globs {
-		if !filepath.IsAbs(g) {
-			g = filepath.Join(dir, g)
-		}
-		g, err = execext.Expand(g)
-		if err != nil {
-			return nil, err
-		}
-		f, err := zglob.Glob(g)
+		f, err := glob(dir, g)
 		if err != nil {
 			continue
 		}
 		files = append(files, f...)
 	}
 	sort.Strings(files)
-	return
+	return files, nil
+}
+
+func glob(dir string, g string) ([]string, error) {
+	files := make([]string, 0)
+	if !filepath.IsAbs(g) {
+		g = filepath.Join(dir, g)
+	}
+	g, err := execext.Expand(g)
+	if err != nil {
+		return nil, err
+	}
+	fs, err := zglob.Glob(g)
+	if err != nil {
+		return nil, err
+	}
+	for _, f := range fs {
+		info, err := os.Stat(f)
+		if err != nil {
+			return nil, err
+		}
+		if info.IsDir() {
+			continue
+		}
+		files = append(files, f)
+	}
+	return files, nil
 }
diff --git a/internal/status/timestamp.go b/internal/status/timestamp.go
index 62b9aafb..fcc52f6a 100644
--- a/internal/status/timestamp.go
+++ b/internal/status/timestamp.go
@@ -19,11 +19,11 @@ func (t *Timestamp) IsUpToDate() (bool, error) {
 		return false, nil
 	}
 
-	sources, err := glob(t.Dir, t.Sources)
+	sources, err := globs(t.Dir, t.Sources)
 	if err != nil {
 		return false, nil
 	}
-	generates, err := glob(t.Dir, t.Generates)
+	generates, err := globs(t.Dir, t.Generates)
 	if err != nil {
 		return false, nil
 	}
diff --git a/status.go b/status.go
index 7ebb5f84..51d0e4cb 100644
--- a/status.go
+++ b/status.go
@@ -58,10 +58,11 @@ func (e *Executor) getStatusChecker(t *taskfile.Task) (status.Checker, error) {
 		}, nil
 	case "checksum":
 		return &status.Checksum{
-			Dir:     t.Dir,
-			Task:    t.Task,
-			Sources: t.Sources,
-			Dry:     e.Dry,
+			Dir:       t.Dir,
+			Task:      t.Task,
+			Sources:   t.Sources,
+			Generates: t.Generates,
+			Dry:       e.Dry,
 		}, nil
 	case "none":
 		return status.None{}, nil