diff --git a/pkg/cmd/pr/checks/checks.go b/pkg/cmd/pr/checks/checks.go
index 65df87b15..fb629d497 100644
--- a/pkg/cmd/pr/checks/checks.go
+++ b/pkg/cmd/pr/checks/checks.go
@@ -30,6 +30,7 @@ type ChecksOptions struct {
 	WebMode     bool
 	Interval    time.Duration
 	Watch       bool
+	FailFast    bool
 	Required    bool
 }
 
@@ -59,6 +60,10 @@ func NewCmdChecks(f *cmdutil.Factory, runF func(*ChecksOptions) error) *cobra.Co
 				return cmdutil.FlagErrorf("argument required when using the `--repo` flag")
 			}
 
+			if opts.FailFast && !opts.Watch {
+				return cmdutil.FlagErrorf("cannot use `--fail-fast` flag without `--watch` flag")
+			}
+
 			intervalChanged := cmd.Flags().Changed("interval")
 			if !opts.Watch && intervalChanged {
 				return cmdutil.FlagErrorf("cannot use `--interval` flag without `--watch` flag")
@@ -86,6 +91,7 @@ func NewCmdChecks(f *cmdutil.Factory, runF func(*ChecksOptions) error) *cobra.Co
 
 	cmd.Flags().BoolVarP(&opts.WebMode, "web", "w", false, "Open the web browser to show details about checks")
 	cmd.Flags().BoolVarP(&opts.Watch, "watch", "", false, "Watch checks until they finish")
+	cmd.Flags().BoolVarP(&opts.FailFast, "fail-fast", "", false, "Exit watch mode on first check failure")
 	cmd.Flags().IntVarP(&interval, "interval", "i", 10, "Refresh interval in seconds when using `--watch` flag")
 	cmd.Flags().BoolVar(&opts.Required, "required", false, "Only show checks that are required")
 
@@ -171,6 +177,10 @@ func checksRun(opts *ChecksOptions) error {
 			break
 		}
 
+		if opts.FailFast && counts.Failed > 0 {
+			break
+		}
+
 		time.Sleep(opts.Interval)
 
 		checks, counts, err = populateStatusChecks(client, repo, pr, opts.Required)
diff --git a/pkg/cmd/pr/checks/checks_test.go b/pkg/cmd/pr/checks/checks_test.go
index 3e5c8394a..186c1d324 100644
--- a/pkg/cmd/pr/checks/checks_test.go
+++ b/pkg/cmd/pr/checks/checks_test.go
@@ -62,6 +62,20 @@ func TestNewCmdChecks(t *testing.T) {
 			cli:        "--interval 5",
 			wantsError: "cannot use `--interval` flag without `--watch` flag",
 		},
+		{
+			name: "watch with fail-fast flag",
+			cli:  "--watch --fail-fast",
+			wants: ChecksOptions{
+				Watch:    true,
+				FailFast: true,
+				Interval: time.Duration(10000000000),
+			},
+		},
+		{
+			name:       "fail-fast flag without watch flag",
+			cli:        "--fail-fast",
+			wantsError: "cannot use `--fail-fast` flag without `--watch` flag",
+		},
 		{
 			name: "required flag",
 			cli:  "--required",
@@ -102,6 +116,7 @@ func TestNewCmdChecks(t *testing.T) {
 			assert.Equal(t, tt.wants.Watch, gotOpts.Watch)
 			assert.Equal(t, tt.wants.Interval, gotOpts.Interval)
 			assert.Equal(t, tt.wants.Required, gotOpts.Required)
+			assert.Equal(t, tt.wants.FailFast, gotOpts.FailFast)
 		})
 	}
 }
@@ -111,6 +126,7 @@ func Test_checksRun(t *testing.T) {
 		name      string
 		tty       bool
 		watch     bool
+		failFast  bool
 		required  bool
 		httpStubs func(*httpmock.Registry)
 		wantOut   string
@@ -189,6 +205,20 @@ func Test_checksRun(t *testing.T) {
 			wantOut: "\x1b[?1049hAll checks were successful\n0 failing, 3 successful, 0 skipped, and 0 pending checks\n\n✓  awesome tests  1m26s  sweet link\n✓  cool tests     1m26s  sweet link\n✓  rad tests      1m26s  sweet link\n\x1b[?1049lAll checks were successful\n0 failing, 3 successful, 0 skipped, and 0 pending checks\n\n✓  awesome tests  1m26s  sweet link\n✓  cool tests     1m26s  sweet link\n✓  rad tests      1m26s  sweet link\n",
 			wantErr: "",
 		},
+		{
+			name:     "watch some failing with fail fast",
+			tty:      true,
+			watch:    true,
+			failFast: true,
+			httpStubs: func(reg *httpmock.Registry) {
+				reg.Register(
+					httpmock.GraphQL(`query PullRequestStatusChecks\b`),
+					httpmock.FileResponse("./fixtures/someFailing.json"),
+				)
+			},
+			wantOut: "\x1b[?1049h\x1b[0;0H\x1b[JRefreshing checks status every 0 seconds. Press Ctrl+C to quit.\n\nSome checks were not successful\n1 failing, 1 successful, 0 skipped, and 1 pending checks\n\nX  sad tests   1m26s  sweet link\n✓  cool tests  1m26s  sweet link\n*  slow tests  1m26s  sweet link\n\x1b[?1049lSome checks were not successful\n1 failing, 1 successful, 0 skipped, and 1 pending checks\n\nX  sad tests   1m26s  sweet link\n✓  cool tests  1m26s  sweet link\n*  slow tests  1m26s  sweet link\n",
+			wantErr: "SilentError",
+		},
 		{
 			name: "with statuses",
 			tty:  true,
@@ -316,6 +346,7 @@ func Test_checksRun(t *testing.T) {
 				SelectorArg: "123",
 				Finder:      shared.NewMockFinder("123", response, ghrepo.New("OWNER", "REPO")),
 				Watch:       tt.watch,
+				FailFast:    tt.failFast,
 				Required:    tt.required,
 			}
 
@@ -381,7 +412,7 @@ func TestChecksRun_web(t *testing.T) {
 	}
 }
 
-func TestEliminateDupulicates(t *testing.T) {
+func TestEliminateDuplicates(t *testing.T) {
 	tests := []struct {
 		name          string
 		checkContexts []api.CheckContext