diff --git a/api/auth/validate_oauth.go b/api/auth/validate_oauth.go
index a941050ee..5a31c0069 100644
--- a/api/auth/validate_oauth.go
+++ b/api/auth/validate_oauth.go
@@ -1,6 +1,4 @@
-// Copyright (c) 2023 Target Brands, Inc. All rights reserved.
-//
-// Use of this source code is governed by the LICENSE file in this repository.
+// SPDX-License-Identifier: Apache-2.0
 
 package auth
 
diff --git a/api/build/auto_cancel.go b/api/build/auto_cancel.go
new file mode 100644
index 000000000..975306f8c
--- /dev/null
+++ b/api/build/auto_cancel.go
@@ -0,0 +1,181 @@
+// SPDX-License-Identifier: Apache-2.0
+
+package build
+
+import (
+	"context"
+	"encoding/json"
+	"fmt"
+	"io"
+	"net/http"
+	"strings"
+	"time"
+
+	"github.com/gin-gonic/gin"
+	"github.com/go-vela/server/database"
+	"github.com/go-vela/server/internal/token"
+	"github.com/go-vela/types/constants"
+	"github.com/go-vela/types/library"
+	"github.com/go-vela/types/pipeline"
+)
+
+// AutoCancel is a helper function that checks to see if any pending or running
+// builds for the repo can be replaced by the current build.
+func AutoCancel(c *gin.Context, b *library.Build, rB *library.Build, r *library.Repo, cancelOpts *pipeline.CancelOptions) (bool, error) {
+	// if build is the current build, continue
+	if rB.GetID() == b.GetID() {
+		return false, nil
+	}
+
+	// ensure criteria is met before auto canceling (push to same branch, or pull with same action from same head_ref)
+	if (strings.EqualFold(rB.GetEvent(), constants.EventPush) &&
+		strings.EqualFold(b.GetEvent(), constants.EventPush) &&
+		strings.EqualFold(b.GetBranch(), rB.GetBranch())) ||
+		(strings.EqualFold(rB.GetEvent(), constants.EventPull) &&
+			strings.EqualFold(b.GetEventAction(), rB.GetEventAction()) &&
+			strings.EqualFold(b.GetHeadRef(), rB.GetHeadRef())) {
+		switch {
+		case strings.EqualFold(rB.GetStatus(), constants.StatusPending) && cancelOpts.Pending:
+			// pending build will be handled gracefully by worker once pulled off queue
+			rB.SetStatus(constants.StatusCanceled)
+
+			_, err := database.FromContext(c).UpdateBuild(c, rB)
+			if err != nil {
+				return false, err
+			}
+		case strings.EqualFold(rB.GetStatus(), constants.StatusRunning) && cancelOpts.Running:
+			// call cancelRunning routine for builds already running on worker
+			err := cancelRunning(c, rB, r)
+			if err != nil {
+				return false, err
+			}
+		default:
+			return false, nil
+		}
+
+		// set error message that references current build
+		rB.SetError(fmt.Sprintf("build was auto canceled in favor of build %d", b.GetNumber()))
+
+		_, err := database.FromContext(c).UpdateBuild(c, rB)
+		if err != nil {
+			// if this call fails, we still canceled the build, so return true
+			return true, err
+		}
+	}
+
+	return true, nil
+}
+
+// cancelRunning is a helper function that determines the executor currently running a build and sends an API call
+// to that executor's worker to cancel the build.
+func cancelRunning(c *gin.Context, b *library.Build, r *library.Repo) error {
+	e := new([]library.Executor)
+	// retrieve the worker
+	w, err := database.FromContext(c).GetWorkerForHostname(c, b.GetHost())
+	if err != nil {
+		return err
+	}
+
+	// prepare the request to the worker to retrieve executors
+	client := http.DefaultClient
+	client.Timeout = 30 * time.Second
+	endpoint := fmt.Sprintf("%s/api/v1/executors", w.GetAddress())
+
+	req, err := http.NewRequestWithContext(context.Background(), "GET", endpoint, nil)
+	if err != nil {
+		return err
+	}
+
+	tm := c.MustGet("token-manager").(*token.Manager)
+
+	// set mint token options
+	mto := &token.MintTokenOpts{
+		Hostname:      "vela-server",
+		TokenType:     constants.WorkerAuthTokenType,
+		TokenDuration: time.Minute * 1,
+	}
+
+	// mint token
+	tkn, err := tm.MintToken(mto)
+	if err != nil {
+		return err
+	}
+
+	// add the token to authenticate to the worker
+	req.Header.Add("Authorization", fmt.Sprintf("Bearer %s", tkn))
+
+	// make the request to the worker and check the response
+	resp, err := client.Do(req)
+	if err != nil {
+		return err
+	}
+
+	defer resp.Body.Close()
+
+	// Read Response Body
+	respBody, err := io.ReadAll(resp.Body)
+	if err != nil {
+		return err
+	}
+
+	// parse response and validate at least one item was returned
+	err = json.Unmarshal(respBody, e)
+	if err != nil {
+		return err
+	}
+
+	for _, executor := range *e {
+		// check each executor on the worker running the build to see if it's running the build we want to cancel
+		if strings.EqualFold(executor.Repo.GetFullName(), r.GetFullName()) && *executor.GetBuild().Number == b.GetNumber() {
+			// prepare the request to the worker
+			client := http.DefaultClient
+			client.Timeout = 30 * time.Second
+
+			// set the API endpoint path we send the request to
+			u := fmt.Sprintf("%s/api/v1/executors/%d/build/cancel", w.GetAddress(), executor.GetID())
+
+			req, err := http.NewRequestWithContext(context.Background(), "DELETE", u, nil)
+			if err != nil {
+				return err
+			}
+
+			tm := c.MustGet("token-manager").(*token.Manager)
+
+			// set mint token options
+			mto := &token.MintTokenOpts{
+				Hostname:      "vela-server",
+				TokenType:     constants.WorkerAuthTokenType,
+				TokenDuration: time.Minute * 1,
+			}
+
+			// mint token
+			tkn, err := tm.MintToken(mto)
+			if err != nil {
+				return err
+			}
+
+			// add the token to authenticate to the worker
+			req.Header.Add("Authorization", fmt.Sprintf("Bearer %s", tkn))
+
+			// perform the request to the worker
+			resp, err := client.Do(req)
+			if err != nil {
+				return err
+			}
+			defer resp.Body.Close()
+
+			// Read Response Body
+			respBody, err := io.ReadAll(resp.Body)
+			if err != nil {
+				return err
+			}
+
+			err = json.Unmarshal(respBody, b)
+			if err != nil {
+				return err
+			}
+		}
+	}
+
+	return nil
+}
diff --git a/api/build/cancel.go b/api/build/cancel.go
index cbc415024..e8cd19264 100644
--- a/api/build/cancel.go
+++ b/api/build/cancel.go
@@ -77,7 +77,7 @@ func CancelBuild(c *gin.Context) {
 	e := executors.Retrieve(c)
 	o := org.Retrieve(c)
 	r := repo.Retrieve(c)
-	u := user.Retrieve(c)
+	user := user.Retrieve(c)
 	ctx := c.Request.Context()
 
 	entry := fmt.Sprintf("%s/%d", r.GetFullName(), b.GetNumber())
@@ -89,7 +89,7 @@ func CancelBuild(c *gin.Context) {
 		"build": b.GetNumber(),
 		"org":   o,
 		"repo":  r.GetName(),
-		"user":  u.GetName(),
+		"user":  user.GetName(),
 	}).Infof("canceling build %s", entry)
 
 	switch b.GetStatus() {
@@ -169,6 +169,16 @@ func CancelBuild(c *gin.Context) {
 					return
 				}
 
+				b.SetError(fmt.Sprintf("build was canceled by %s", user.GetName()))
+
+				b, err = database.FromContext(c).UpdateBuild(ctx, b)
+				if err != nil {
+					retErr := fmt.Errorf("unable to update status for build %s: %w", entry, err)
+					util.HandleError(c, http.StatusInternalServerError, retErr)
+
+					return
+				}
+
 				c.JSON(resp.StatusCode, b)
 
 				return
diff --git a/api/queue/queue.go b/api/queue/queue.go
index 10946e99c..78d4c170b 100644
--- a/api/queue/queue.go
+++ b/api/queue/queue.go
@@ -1,6 +1,4 @@
-// Copyright (c) 2023 Target Brands, Inc. All rights reserved.
-//
-// Use of this source code is governed by the LICENSE file in this repository.
+// SPDX-License-Identifier: Apache-2.0
 
 package queue
 
diff --git a/api/webhook/post.go b/api/webhook/post.go
index d3c2fa6c4..aa4449194 100644
--- a/api/webhook/post.go
+++ b/api/webhook/post.go
@@ -677,6 +677,40 @@ func PostWebhook(c *gin.Context) {
 		repo,
 		u,
 	)
+
+	// if anything is provided in the auto_cancel metadata, then we start with true
+	runAutoCancel := p.Metadata.AutoCancel.Running || p.Metadata.AutoCancel.Pending || p.Metadata.AutoCancel.DefaultBranch
+
+	// if the event is a push to the default branch and the AutoCancel.DefaultBranch value is false, bypass auto cancel
+	if strings.EqualFold(b.GetEvent(), constants.EventPush) && strings.EqualFold(b.GetBranch(), repo.GetBranch()) && !p.Metadata.AutoCancel.DefaultBranch {
+		runAutoCancel = false
+	}
+
+	// if event is push or pull_request:synchronize, there is a chance this build could be superceding a stale build
+	//
+	// fetch pending and running builds for this repo in order to validate their merit to continue running.
+	if runAutoCancel &&
+		((strings.EqualFold(b.GetEvent(), constants.EventPull) && strings.EqualFold(b.GetEventAction(), constants.ActionSynchronize)) ||
+			strings.EqualFold(b.GetEvent(), constants.EventPush)) {
+		// fetch pending and running builds
+		rBs, err := database.FromContext(c).ListPendingAndRunningBuildsForRepo(c, repo)
+		if err != nil {
+			logrus.Errorf("unable to fetch pending and running builds for %s: %v", repo.GetFullName(), err)
+		}
+
+		for _, rB := range rBs {
+			// call auto cancel routine
+			canceled, err := build.AutoCancel(c, b, rB, repo, p.Metadata.AutoCancel)
+			if err != nil {
+				// continue cancel loop if error, but log based on type of error
+				if canceled {
+					logrus.Errorf("unable to update canceled build error message: %v", err)
+				} else {
+					logrus.Errorf("unable to cancel running build: %v", err)
+				}
+			}
+		}
+	}
 }
 
 // handleRepositoryEvent is a helper function that processes repository events from the SCM and updates
diff --git a/database/build/interface.go b/database/build/interface.go
index 3f790ac10..c2b468e39 100644
--- a/database/build/interface.go
+++ b/database/build/interface.go
@@ -58,6 +58,8 @@ type BuildInterface interface {
 	ListBuildsForRepo(context.Context, *library.Repo, map[string]interface{}, int64, int64, int, int) ([]*library.Build, int64, error)
 	// ListPendingAndRunningBuilds defines a function that gets a list of pending and running builds.
 	ListPendingAndRunningBuilds(context.Context, string) ([]*library.BuildQueue, error)
+	// ListPendingAndRunningBuildsForRepo defines a function that gets a list of pending and running builds for a repo.
+	ListPendingAndRunningBuildsForRepo(context.Context, *library.Repo) ([]*library.Build, error)
 	// UpdateBuild defines a function that updates an existing build.
 	UpdateBuild(context.Context, *library.Build) (*library.Build, error)
 }
diff --git a/database/build/list_pending_running_repo.go b/database/build/list_pending_running_repo.go
new file mode 100644
index 000000000..3c82ca419
--- /dev/null
+++ b/database/build/list_pending_running_repo.go
@@ -0,0 +1,45 @@
+// SPDX-License-Identifier: Apache-2.0
+
+package build
+
+import (
+	"context"
+
+	"github.com/go-vela/types/constants"
+	"github.com/go-vela/types/database"
+	"github.com/go-vela/types/library"
+)
+
+// ListPendingAndRunningBuilds gets a list of all pending and running builds in the provided timeframe from the database.
+func (e *engine) ListPendingAndRunningBuildsForRepo(ctx context.Context, repo *library.Repo) ([]*library.Build, error) {
+	e.logger.Trace("listing all pending and running builds from the database")
+
+	// variables to store query results and return value
+	b := new([]database.Build)
+	builds := []*library.Build{}
+
+	// send query to the database and store result in variable
+	err := e.client.
+		Table(constants.TableBuild).
+		Select("*").
+		Where("repo_id = ?", repo.GetID()).
+		Where("status = 'running' OR status = 'pending'").
+		Find(&b).
+		Error
+	if err != nil {
+		return nil, err
+	}
+
+	// iterate through all query results
+	for _, build := range *b {
+		// https://golang.org/doc/faq#closures_and_goroutines
+		tmp := build
+
+		// convert query result to library type
+		//
+		// https://pkg.go.dev/github.com/go-vela/types/database#Build.ToLibrary
+		builds = append(builds, tmp.ToLibrary())
+	}
+
+	return builds, nil
+}
diff --git a/database/build/list_pending_running_repo_test.go b/database/build/list_pending_running_repo_test.go
new file mode 100644
index 000000000..089a6d7b3
--- /dev/null
+++ b/database/build/list_pending_running_repo_test.go
@@ -0,0 +1,148 @@
+// SPDX-License-Identifier: Apache-2.0
+
+package build
+
+import (
+	"context"
+	"reflect"
+	"testing"
+
+	"github.com/DATA-DOG/go-sqlmock"
+	"github.com/go-vela/types/constants"
+	"github.com/go-vela/types/database"
+	"github.com/go-vela/types/library"
+)
+
+func TestBuild_Engine_ListPendingAndRunningBuildsForRepo(t *testing.T) {
+	// setup types
+	_buildOne := testBuild()
+	_buildOne.SetID(1)
+	_buildOne.SetRepoID(1)
+	_buildOne.SetNumber(1)
+	_buildOne.SetStatus("running")
+	_buildOne.SetCreated(1)
+	_buildOne.SetDeployPayload(nil)
+
+	_buildTwo := testBuild()
+	_buildTwo.SetID(2)
+	_buildTwo.SetRepoID(1)
+	_buildTwo.SetNumber(2)
+	_buildTwo.SetStatus("pending")
+	_buildTwo.SetCreated(1)
+	_buildTwo.SetDeployPayload(nil)
+
+	_buildThree := testBuild()
+	_buildThree.SetID(3)
+	_buildThree.SetRepoID(2)
+	_buildThree.SetNumber(1)
+	_buildThree.SetStatus("pending")
+	_buildThree.SetCreated(1)
+	_buildThree.SetDeployPayload(nil)
+
+	_repo := testRepo()
+	_repo.SetID(1)
+	_repo.SetUserID(1)
+	_repo.SetHash("baz")
+	_repo.SetOrg("foo")
+	_repo.SetName("bar")
+	_repo.SetFullName("foo/bar")
+	_repo.SetVisibility("public")
+
+	_repoTwo := testRepo()
+	_repoTwo.SetID(2)
+	_repoTwo.SetUserID(1)
+	_repoTwo.SetHash("bazzy")
+	_repoTwo.SetOrg("foo")
+	_repoTwo.SetName("baz")
+	_repoTwo.SetFullName("foo/baz")
+	_repoTwo.SetVisibility("public")
+
+	_postgres, _mock := testPostgres(t)
+	defer func() { _sql, _ := _postgres.client.DB(); _sql.Close() }()
+
+	// create expected name query result in mock
+	_rows := sqlmock.NewRows(
+		[]string{"id", "repo_id", "pipeline_id", "number", "parent", "event", "event_action", "status", "error", "enqueued", "created", "started", "finished", "deploy", "deploy_payload", "clone", "source", "title", "message", "commit", "sender", "author", "email", "link", "branch", "ref", "base_ref", "head_ref", "host", "runtime", "distribution", "timestamp"}).
+		AddRow(2, 1, nil, 2, 0, "", "", "pending", "", 0, 1, 0, 0, "", nil, "", "", "", "", "", "", "", "", "", "", "", "", "", "", "", "", 0).
+		AddRow(1, 1, nil, 1, 0, "", "", "running", "", 0, 1, 0, 0, "", nil, "", "", "", "", "", "", "", "", "", "", "", "", "", "", "", "", 0)
+
+	// ensure the mock expects the name query
+	_mock.ExpectQuery(`SELECT * FROM "builds" WHERE repo_id = $1 AND (status = 'running' OR status = 'pending')`).WithArgs(1).WillReturnRows(_rows)
+
+	_sqlite := testSqlite(t)
+	defer func() { _sql, _ := _sqlite.client.DB(); _sql.Close() }()
+
+	_, err := _sqlite.CreateBuild(context.TODO(), _buildOne)
+	if err != nil {
+		t.Errorf("unable to create test build for sqlite: %v", err)
+	}
+
+	_, err = _sqlite.CreateBuild(context.TODO(), _buildTwo)
+	if err != nil {
+		t.Errorf("unable to create test build for sqlite: %v", err)
+	}
+
+	_, err = _sqlite.CreateBuild(context.TODO(), _buildThree)
+	if err != nil {
+		t.Errorf("unable to create test build for sqlite: %v", err)
+	}
+
+	err = _sqlite.client.AutoMigrate(&database.Repo{})
+	if err != nil {
+		t.Errorf("unable to create repo table for sqlite: %v", err)
+	}
+
+	err = _sqlite.client.Table(constants.TableRepo).Create(database.RepoFromLibrary(_repo)).Error
+	if err != nil {
+		t.Errorf("unable to create test repo for sqlite: %v", err)
+	}
+
+	err = _sqlite.client.Table(constants.TableRepo).Create(database.RepoFromLibrary(_repoTwo)).Error
+	if err != nil {
+		t.Errorf("unable to create test repo for sqlite: %v", err)
+	}
+
+	// setup tests
+	tests := []struct {
+		failure  bool
+		name     string
+		database *engine
+		want     []*library.Build
+	}{
+		{
+			failure:  false,
+			name:     "postgres",
+			database: _postgres,
+			want:     []*library.Build{_buildTwo, _buildOne},
+		},
+		{
+			failure:  false,
+			name:     "sqlite3",
+			database: _sqlite,
+			want:     []*library.Build{_buildOne, _buildTwo},
+		},
+	}
+
+	// run tests
+	for _, test := range tests {
+		t.Run(test.name, func(t *testing.T) {
+			got, err := test.database.ListPendingAndRunningBuildsForRepo(context.TODO(), _repo)
+
+			if test.failure {
+				if err == nil {
+					t.Errorf("ListPendingAndRunningBuildsForRepo for %s should have returned err", test.name)
+				}
+
+				return
+			}
+
+			if err != nil {
+				t.Errorf("ListPendingAndRunningBuildsForRepo for %s returned err: %v", test.name, err)
+			}
+
+			if !reflect.DeepEqual(got, test.want) {
+				t.Errorf("ListPendingAndRunningBuildsForRepo for %s is %v, want %v", test.name, got, test.want)
+			}
+		})
+	}
+}
diff --git a/database/integration_test.go b/database/integration_test.go
index bcf2fcd7f..b30176004 100644
--- a/database/integration_test.go
+++ b/database/integration_test.go
@@ -296,6 +296,19 @@ func testBuilds(t *testing.T, db Interface, resources *Resources) {
 	}
 	methods["ListBuildsForRepo"] = true
 
+	// list the pending / running builds for a repo
+	list, err = db.ListPendingAndRunningBuildsForRepo(context.TODO(), resources.Repos[0])
+	if err != nil {
+		t.Errorf("unable to list pending and running builds for repo %d: %v", resources.Repos[0].GetID(), err)
+	}
+	if int(count) != len(resources.Builds) {
+		t.Errorf("ListPendingAndRunningBuildsForRepo() is %v, want %v", count, len(resources.Builds))
+	}
+	if !cmp.Equal(list, []*library.Build{resources.Builds[0], resources.Builds[1]}) {
+		t.Errorf("ListPendingAndRunningBuildsForRepo() is %v, want %v", list, []*library.Build{resources.Builds[0], resources.Builds[1]})
+	}
+	methods["ListPendingAndRunningBuildsForRepo"] = true
+
 	// list the pending and running builds
 	queueList, err := db.ListPendingAndRunningBuilds(context.TODO(), "0")
 	if err != nil {
diff --git a/database/resource.go b/database/resource.go
index 353f25513..35f7c7a97 100644
--- a/database/resource.go
+++ b/database/resource.go
@@ -1,6 +1,4 @@
-// Copyright (c) 2023 Target Brands, Ine. All rights reserved.
-//
-// Use of this source code is governed by the LICENSE file in this repository.
+// SPDX-License-Identifier: Apache-2.0
 
 package database
 
diff --git a/database/validate.go b/database/validate.go
index 18f07cb84..4c519d081 100644
--- a/database/validate.go
+++ b/database/validate.go
@@ -1,6 +1,4 @@
-// Copyright (c) 2023 Target Brands, Ine. All rights reserved.
-//
-// Use of this source code is governed by the LICENSE file in this repository.
+// SPDX-License-Identifier: Apache-2.0
 
 package database
 
diff --git a/database/validate_test.go b/database/validate_test.go
index 60761e215..36b60fb98 100644
--- a/database/validate_test.go
+++ b/database/validate_test.go
@@ -1,6 +1,4 @@
-// Copyright (c) 2023 Target Brands, Ine. All rights reserved.
-//
-// Use of this source code is governed by the LICENSE file in this repository.
+// SPDX-License-Identifier: Apache-2.0
 
 package database
 
diff --git a/router/middleware/signing_test.go b/router/middleware/signing_test.go
index 908c0908b..3f152a3c9 100644
--- a/router/middleware/signing_test.go
+++ b/router/middleware/signing_test.go
@@ -1,6 +1,4 @@
-// Copyright (c) 2023 Target Brands, Inc. All rights reserved.
-//
-// Use of this source code is governed by the LICENSE file in this repository.
+// SPDX-License-Identifier: Apache-2.0
 
 package middleware
 
diff --git a/router/queue.go b/router/queue.go
index d3b311b13..ca408ffe3 100644
--- a/router/queue.go
+++ b/router/queue.go
@@ -1,6 +1,4 @@
-// Copyright (c) 2023 Target Brands, Inc. All rights reserved.
-//
-// Use of this source code is governed by the LICENSE file in this repository.
+// SPDX-License-Identifier: Apache-2.0
 
 package router