diff --git a/errand-routes.go b/errand-routes.go
index 67a52c0..cc4cf8e 100644
--- a/errand-routes.go
+++ b/errand-routes.go
@@ -84,27 +84,7 @@ func (s *ErrandsServer) failedErrand(c *gin.Context) {
 	}
 
 	updatedErrand, err := s.UpdateErrandByID(c.Param("id"), func(errand *schemas.Errand) error {
-		// Update this errand attributes:
-		if err := errand.AddToLogs("ERROR", failedReq.Reason); err != nil {
-			return err
-		}
-		errand.Failed = utils.GetTimestamp()
-		errand.Status = schemas.StatusFailed
-		errand.Progress = 0
-		if errand.Options.Retries > 0 {
-			// If we should retry this errand:
-			if errand.Attempts <= errand.Options.Retries {
-				errand.Status = inactive
-			} else {
-				// If this errand is out of retries
-				metrics.ErrandFailed(errand.Type)
-			}
-		} else {
-			// If this errand was not configured with retries
-			metrics.ErrandFailed(errand.Type)
-		}
-
-		return nil
+		return failErrand(errand, failedReq)
 	})
 	if err != nil {
 		c.JSON(http.StatusInternalServerError, gin.H{
@@ -122,6 +102,30 @@ func (s *ErrandsServer) failedErrand(c *gin.Context) {
 	})
 }
 
+func failErrand(errand *schemas.Errand, failureRequest FailedRequest) error {
+	// Update this errand attributes:
+	if err := errand.AddToLogs("ERROR", failureRequest.Reason); err != nil {
+		return err
+	}
+	errand.Failed = utils.GetTimestamp()
+	errand.Status = schemas.StatusFailed
+	errand.Progress = 0
+	if errand.Options.Retries > 0 {
+		// If we should retry this errand:
+		if errand.Attempts <= errand.Options.Retries {
+			errand.Status = inactive
+		} else {
+			// If this errand is out of retries
+			metrics.ErrandFailed(errand.Type)
+		}
+	} else {
+		// If this errand was not configured with retries
+		metrics.ErrandFailed(errand.Type)
+	}
+
+	return nil
+}
+
 type CompletedRequest struct {
 	Results *gin.H `json:"results"`
 }
@@ -256,14 +260,14 @@ func (s *ErrandsServer) deleteErrandByID(id string) {
 }
 
 // UpdateErrandByID Lets you pass in a function which will be called allowing you to update the errand. If no error is returned, the errand will be saved in the DB with the new attributes.
-func (s *ErrandsServer) UpdateErrandByID(id string, fn func(*schemas.Errand) error) (*schemas.Errand, error) {
+func (s *ErrandsServer) UpdateErrandByID(id string, update func(*schemas.Errand) error) (*schemas.Errand, error) {
 	errandObj, found := s.ErrandStore.Get(id)
 	if !found {
 		return nil, errors.New("errand with this ID not found")
 	}
 
 	errand := errandObj.(schemas.Errand)
-	if err := fn(&errand); err != nil {
+	if err := update(&errand); err != nil {
 		return nil, fmt.Errorf("error in given update function (fn): %w", err)
 	}
 
@@ -273,3 +277,21 @@ func (s *ErrandsServer) UpdateErrandByID(id string, fn func(*schemas.Errand) err
 
 	return &errand, nil
 }
+
+func (s *ErrandsServer) UpdateErrandsByFilter(filter func(*schemas.Errand) bool, update func(*schemas.Errand) error) error {
+	for _, itemObj := range s.ErrandStore.Items() {
+		errand := itemObj.Object.(schemas.Errand)
+
+		if filter(&errand) {
+			if err := update(&errand); err != nil {
+				return fmt.Errorf("error in given update function (fn): %w", err)
+			}
+
+			s.updateErrandInPipeline(&errand)
+
+			s.ErrandStore.SetDefault(errand.ID, errand)
+		}
+	}
+
+	return nil
+}
diff --git a/errands-server.go b/errands-server.go
index 9c48f17..c6c0180 100644
--- a/errands-server.go
+++ b/errands-server.go
@@ -1,6 +1,7 @@
 package main
 
 import (
+	"fmt"
 	"net/http"
 	"path"
 	"reflect"
@@ -77,6 +78,8 @@ func NewErrandsServer(cfg *Config) *ErrandsServer {
 
 	go obj.periodicallySaveDB()
 
+	go obj.periodicallyCheckTTLs()
+
 	return obj
 }
 
@@ -93,6 +96,37 @@ func (s *ErrandsServer) periodicallySaveDB() {
 	}
 }
 
+func (s *ErrandsServer) periodicallyCheckTTLs() {
+	t := time.NewTicker(time.Minute)
+	defer t.Stop()
+
+	filter := func(errand *schemas.Errand) bool {
+		if errand.Options.TTL <= 0 {
+			return false
+		}
+
+		started := time.Unix(0, errand.Started*1_000_000)              // ms to ns
+		ttlDuration := time.Duration(errand.Options.TTL) * time.Minute // m to ns
+
+		return time.Since(started) > ttlDuration
+	}
+
+	update := func(errand *schemas.Errand) error {
+		if err := failErrand(errand, FailedRequest{Reason: "TTL Expired"}); err != nil {
+			return fmt.Errorf("unable to fail errand: %s; %w", errand.ID, err)
+		}
+
+		s.AddNotification("failed", errand)
+		return nil
+	}
+
+	for range t.C {
+		if err := s.UpdateErrandsByFilter(filter, update); err != nil {
+			log.WithError(err).Error("Unable to fail errand(s)")
+		}
+	}
+}
+
 func (s *ErrandsServer) saveDBs() {
 	if err := s.ErrandStore.SaveFile(path.Join(s.StorageDir, errandsDBPathSuffix)); err != nil {
 		log.Error("----- Error checkpoint saving the errand DB to file -----")
diff --git a/schemas/errand.go b/schemas/errand.go
index 2c47ea9..0086ff3 100644
--- a/schemas/errand.go
+++ b/schemas/errand.go
@@ -3,7 +3,6 @@ package schemas
 
 import (
 	"fmt"
-
 	"github.com/google/uuid"
 
 	"github.com/polygon-io/errands-server/utils"
@@ -51,6 +50,7 @@ type Errand struct {
 // ErrandOptions holds various options tied to an errand.
 //easyjson:json
 type ErrandOptions struct {
+	// TTL is measured in minutes.
 	TTL               int  `json:"ttl,omitempty"`
 	Retries           int  `json:"retries,omitempty"`
 	Priority          int  `json:"priority,omitempty"`