diff --git a/.github/workflows/coder.yaml b/.github/workflows/coder.yaml
index fb41b3f1f2924..a0e4b6a7e905a 100644
--- a/.github/workflows/coder.yaml
+++ b/.github/workflows/coder.yaml
@@ -269,7 +269,11 @@ jobs:
             echo ::set-output name=cover::false
           fi
           set -x
-          gotestsum --junitfile="gotests.xml" --packages="./..." -- -parallel=8 -timeout=5m -short -failfast $COVERAGE_FLAGS
+          test_timeout=5m
+          if [[ "${{ matrix.os }}" == windows* ]]; then
+            test_timeout=10m
+          fi
+          gotestsum --junitfile="gotests.xml" --packages="./..." -- -parallel=8 -timeout=$test_timeout -short -failfast $COVERAGE_FLAGS
 
       - name: Upload DataDog Trace
         if: github.actor != 'dependabot[bot]' && !github.event.pull_request.head.repo.fork
diff --git a/agent/agent_test.go b/agent/agent_test.go
index cefa54d037f31..e3d3a80886c02 100644
--- a/agent/agent_test.go
+++ b/agent/agent_test.go
@@ -38,6 +38,7 @@ import (
 	"github.com/coder/coder/peerbroker/proto"
 	"github.com/coder/coder/provisionersdk"
 	"github.com/coder/coder/pty/ptytest"
+	"github.com/coder/coder/testutil"
 )
 
 func TestMain(m *testing.M) {
@@ -257,7 +258,7 @@ func TestAgent(t *testing.T) {
 			}
 			gotContent = string(content)
 			return true
-		}, 15*time.Second, 100*time.Millisecond)
+		}, testutil.WaitMedium, testutil.IntervalMedium)
 		require.Equal(t, content, strings.TrimSpace(gotContent))
 	})
 
diff --git a/agent/reaper/reaper_test.go b/agent/reaper/reaper_test.go
index 8e23bec198c5c..88573636ee39c 100644
--- a/agent/reaper/reaper_test.go
+++ b/agent/reaper/reaper_test.go
@@ -12,6 +12,7 @@ import (
 	"github.com/stretchr/testify/require"
 
 	"github.com/coder/coder/agent/reaper"
+	"github.com/coder/coder/testutil"
 )
 
 func TestReap(t *testing.T) {
@@ -52,10 +53,9 @@ func TestReap(t *testing.T) {
 
 		expectedPIDs := []int{cmd.Process.Pid, cmd2.Process.Pid}
 
-		deadline := time.NewTimer(time.Second * 5)
 		for i := 0; i < len(expectedPIDs); i++ {
 			select {
-			case <-deadline.C:
+			case <-time.After(testutil.WaitShort):
 				t.Fatalf("Timed out waiting for process")
 			case pid := <-pids:
 				require.Contains(t, expectedPIDs, pid)
diff --git a/cli/cliui/prompt_test.go b/cli/cliui/prompt_test.go
index eefc6ab4c8a5a..6c7f233c872e6 100644
--- a/cli/cliui/prompt_test.go
+++ b/cli/cliui/prompt_test.go
@@ -7,7 +7,6 @@ import (
 	"os"
 	"os/exec"
 	"testing"
-	"time"
 
 	"github.com/spf13/cobra"
 	"github.com/stretchr/testify/assert"
@@ -16,6 +15,7 @@ import (
 	"github.com/coder/coder/cli/cliui"
 	"github.com/coder/coder/pty"
 	"github.com/coder/coder/pty/ptytest"
+	"github.com/coder/coder/testutil"
 )
 
 func TestPrompt(t *testing.T) {
@@ -61,7 +61,7 @@ func TestPrompt(t *testing.T) {
 		// Copy all data written out to a buffer. When we close the ptty, we can
 		// no longer read from the ptty.Output(), but we can read what was
 		// written to the buffer.
-		dataRead, doneReading := context.WithTimeout(context.Background(), time.Second*2)
+		dataRead, doneReading := context.WithTimeout(context.Background(), testutil.WaitShort)
 		go func() {
 			// This will throw an error sometimes. The underlying ptty
 			// has its own cleanup routines in t.Cleanup. Instead of
@@ -193,7 +193,7 @@ func TestPasswordTerminalState(t *testing.T) {
 	require.Eventually(t, func() bool {
 		echo, err := ptyWithFlags.EchoEnabled()
 		return err == nil && !echo
-	}, 5*time.Second, 50*time.Millisecond, "echo is on while reading password")
+	}, testutil.WaitShort, testutil.IntervalMedium, "echo is on while reading password")
 
 	err = process.Signal(os.Interrupt)
 	require.NoError(t, err)
@@ -203,7 +203,7 @@ func TestPasswordTerminalState(t *testing.T) {
 	require.Eventually(t, func() bool {
 		echo, err := ptyWithFlags.EchoEnabled()
 		return err == nil && echo
-	}, 5*time.Second, 50*time.Millisecond, "echo is off after reading password")
+	}, testutil.WaitShort, testutil.IntervalMedium, "echo is off after reading password")
 }
 
 // nolint:unused
diff --git a/cli/create_test.go b/cli/create_test.go
index 5578518f351dc..cdb8f5e5e8019 100644
--- a/cli/create_test.go
+++ b/cli/create_test.go
@@ -16,6 +16,7 @@ import (
 	"github.com/coder/coder/provisioner/echo"
 	"github.com/coder/coder/provisionersdk/proto"
 	"github.com/coder/coder/pty/ptytest"
+	"github.com/coder/coder/testutil"
 )
 
 func TestCreate(t *testing.T) {
@@ -88,7 +89,7 @@ func TestCreate(t *testing.T) {
 
 		member := coderdtest.CreateAnotherUser(t, client, user.OrganizationID)
 		clitest.SetupConfig(t, member, root)
-		cmdCtx, done := context.WithTimeout(context.Background(), 10*time.Second)
+		cmdCtx, done := context.WithTimeout(context.Background(), testutil.WaitLong)
 		go func() {
 			defer done()
 			err := cmd.ExecuteContext(cmdCtx)
diff --git a/cli/list_test.go b/cli/list_test.go
index 8343f1fead1ab..a5aaeb5f4da30 100644
--- a/cli/list_test.go
+++ b/cli/list_test.go
@@ -3,13 +3,13 @@ package cli_test
 import (
 	"context"
 	"testing"
-	"time"
 
 	"github.com/stretchr/testify/assert"
 
 	"github.com/coder/coder/cli/clitest"
 	"github.com/coder/coder/coderd/coderdtest"
 	"github.com/coder/coder/pty/ptytest"
+	"github.com/coder/coder/testutil"
 )
 
 func TestList(t *testing.T) {
@@ -29,7 +29,7 @@ func TestList(t *testing.T) {
 		cmd.SetIn(pty.Input())
 		cmd.SetOut(pty.Output())
 
-		ctx, cancelFunc := context.WithTimeout(context.Background(), 5*time.Second)
+		ctx, cancelFunc := context.WithTimeout(context.Background(), testutil.WaitLong)
 		defer cancelFunc()
 		done := make(chan any)
 		go func() {
diff --git a/cli/portforward_test.go b/cli/portforward_test.go
index 5f314a3658850..a3547ba4dface 100644
--- a/cli/portforward_test.go
+++ b/cli/portforward_test.go
@@ -23,6 +23,7 @@ import (
 	"github.com/coder/coder/codersdk"
 	"github.com/coder/coder/provisioner/echo"
 	"github.com/coder/coder/provisionersdk/proto"
+	"github.com/coder/coder/testutil"
 )
 
 func TestPortForward(t *testing.T) {
@@ -170,7 +171,7 @@ func TestPortForward(t *testing.T) {
 
 				// Open two connections simultaneously and test them out of
 				// sync.
-				d := net.Dialer{Timeout: 3 * time.Second}
+				d := net.Dialer{Timeout: testutil.WaitShort}
 				c1, err := d.DialContext(ctx, c.network, localAddress)
 				require.NoError(t, err, "open connection 1 to 'local' listener")
 				defer c1.Close()
@@ -216,7 +217,7 @@ func TestPortForward(t *testing.T) {
 
 				// Open a connection to both listener 1 and 2 simultaneously and
 				// then test them out of order.
-				d := net.Dialer{Timeout: 3 * time.Second}
+				d := net.Dialer{Timeout: testutil.WaitShort}
 				c1, err := d.DialContext(ctx, c.network, localAddress1)
 				require.NoError(t, err, "open connection 1 to 'local' listener 1")
 				defer c1.Close()
@@ -269,7 +270,7 @@ func TestPortForward(t *testing.T) {
 
 		// Open two connections simultaneously and test them out of
 		// sync.
-		d := net.Dialer{Timeout: 3 * time.Second}
+		d := net.Dialer{Timeout: testutil.WaitShort}
 		c1, err := d.DialContext(ctx, tcpCase.network, localAddress)
 		require.NoError(t, err, "open connection 1 to 'local' listener")
 		defer c1.Close()
@@ -329,7 +330,7 @@ func TestPortForward(t *testing.T) {
 
 		// Open connections to all items in the "dial" array.
 		var (
-			d     = net.Dialer{Timeout: 3 * time.Second}
+			d     = net.Dialer{Timeout: testutil.WaitShort}
 			conns = make([]net.Conn, len(dials))
 		)
 		for i, a := range dials {
@@ -488,7 +489,7 @@ func assertWritePayload(t *testing.T, w io.Writer, payload []byte) {
 func waitForPortForwardReady(t *testing.T, output *threadSafeBuffer) {
 	t.Helper()
 	for i := 0; i < 100; i++ {
-		time.Sleep(250 * time.Millisecond)
+		time.Sleep(testutil.IntervalMedium)
 
 		data := output.String()
 		if strings.Contains(data, "Ready!") {
diff --git a/cli/resetpassword_test.go b/cli/resetpassword_test.go
index 6499e30a2481b..420f3793b2f09 100644
--- a/cli/resetpassword_test.go
+++ b/cli/resetpassword_test.go
@@ -5,7 +5,6 @@ import (
 	"net/url"
 	"runtime"
 	"testing"
-	"time"
 
 	"github.com/stretchr/testify/assert"
 	"github.com/stretchr/testify/require"
@@ -14,6 +13,7 @@ import (
 	"github.com/coder/coder/coderd/database/postgres"
 	"github.com/coder/coder/codersdk"
 	"github.com/coder/coder/pty/ptytest"
+	"github.com/coder/coder/testutil"
 )
 
 // nolint:paralleltest
@@ -53,7 +53,7 @@ func TestResetPassword(t *testing.T) {
 	require.Eventually(t, func() bool {
 		rawURL, err = cfg.URL().Read()
 		return err == nil && rawURL != ""
-	}, 15*time.Second, 25*time.Millisecond)
+	}, testutil.WaitLong, testutil.IntervalFast)
 	accessURL, err := url.Parse(rawURL)
 	require.NoError(t, err)
 	client := codersdk.New(accessURL)
diff --git a/cli/server_test.go b/cli/server_test.go
index 5501ed79b5c33..ed9676f98f391 100644
--- a/cli/server_test.go
+++ b/cli/server_test.go
@@ -25,10 +25,12 @@ import (
 	"go.uber.org/goleak"
 
 	"github.com/coder/coder/cli/clitest"
+	"github.com/coder/coder/cli/config"
 	"github.com/coder/coder/coderd/database/postgres"
 	"github.com/coder/coder/coderd/telemetry"
 	"github.com/coder/coder/codersdk"
 	"github.com/coder/coder/pty/ptytest"
+	"github.com/coder/coder/testutil"
 )
 
 // This cannot be ran in parallel because it uses a signal.
@@ -55,13 +57,7 @@ func TestServer(t *testing.T) {
 		go func() {
 			errC <- root.ExecuteContext(ctx)
 		}()
-		var rawURL string
-		require.Eventually(t, func() bool {
-			rawURL, err = cfg.URL().Read()
-			return err == nil && rawURL != ""
-		}, time.Minute, 50*time.Millisecond)
-		accessURL, err := url.Parse(rawURL)
-		require.NoError(t, err)
+		accessURL := waitAccessURL(t, cfg)
 		client := codersdk.New(accessURL)
 
 		_, err = client.CreateFirstUser(ctx, codersdk.CreateFirstUserRequest{
@@ -94,10 +90,11 @@ func TestServer(t *testing.T) {
 		go func() {
 			errC <- root.ExecuteContext(ctx)
 		}()
+		//nolint:gocritic // Embedded postgres take a while to fire up.
 		require.Eventually(t, func() bool {
-			accessURLRaw, err := cfg.URL().Read()
-			return accessURLRaw != "" && err == nil
-		}, 3*time.Minute, 250*time.Millisecond)
+			rawURL, err := cfg.URL().Read()
+			return err == nil && rawURL != ""
+		}, 3*time.Minute, testutil.IntervalFast, "failed to get access URL")
 		cancelFunc()
 		require.ErrorIs(t, <-errC, context.Canceled)
 	})
@@ -135,11 +132,7 @@ func TestServer(t *testing.T) {
 		}()
 
 		// Just wait for startup
-		require.Eventually(t, func() bool {
-			var err error
-			_, err = cfg.URL().Read()
-			return err == nil
-		}, 15*time.Second, 25*time.Millisecond)
+		_ = waitAccessURL(t, cfg)
 
 		cancelFunc()
 		require.ErrorIs(t, <-errC, context.Canceled)
@@ -169,11 +162,7 @@ func TestServer(t *testing.T) {
 		}()
 
 		// Just wait for startup
-		require.Eventually(t, func() bool {
-			var err error
-			_, err = cfg.URL().Read()
-			return err == nil
-		}, 15*time.Second, 25*time.Millisecond)
+		_ = waitAccessURL(t, cfg)
 
 		cancelFunc()
 		require.ErrorIs(t, <-errC, context.Canceled)
@@ -201,11 +190,7 @@ func TestServer(t *testing.T) {
 		}()
 
 		// Just wait for startup
-		require.Eventually(t, func() bool {
-			var err error
-			_, err = cfg.URL().Read()
-			return err == nil
-		}, 15*time.Second, 25*time.Millisecond)
+		_ = waitAccessURL(t, cfg)
 
 		cancelFunc()
 		require.ErrorIs(t, <-errC, context.Canceled)
@@ -281,14 +266,7 @@ func TestServer(t *testing.T) {
 		}()
 
 		// Verify HTTPS
-		var accessURLRaw string
-		require.Eventually(t, func() bool {
-			var err error
-			accessURLRaw, err = cfg.URL().Read()
-			return accessURLRaw != "" && err == nil
-		}, 15*time.Second, 25*time.Millisecond)
-		accessURL, err := url.Parse(accessURLRaw)
-		require.NoError(t, err)
+		accessURL := waitAccessURL(t, cfg)
 		require.Equal(t, "https", accessURL.Scheme)
 		client := codersdk.New(accessURL)
 		client.HTTPClient = &http.Client{
@@ -299,7 +277,7 @@ func TestServer(t *testing.T) {
 				},
 			},
 		}
-		_, err = client.HasFirstUser(ctx)
+		_, err := client.HasFirstUser(ctx)
 		require.NoError(t, err)
 
 		cancelFunc()
@@ -326,11 +304,7 @@ func TestServer(t *testing.T) {
 		go func() {
 			serverErr <- root.ExecuteContext(ctx)
 		}()
-		require.Eventually(t, func() bool {
-			var err error
-			_, err = cfg.URL().Read()
-			return err == nil
-		}, 15*time.Second, 25*time.Millisecond)
+		_ = waitAccessURL(t, cfg)
 		currentProcess, err := os.FindProcess(os.Getpid())
 		require.NoError(t, err)
 		err = currentProcess.Signal(os.Interrupt)
@@ -436,3 +410,19 @@ func generateTLSCertificate(t testing.TB) (certPath, keyPath string) {
 	require.NoError(t, err)
 	return certFile.Name(), keyFile.Name()
 }
+
+func waitAccessURL(t *testing.T, cfg config.Root) *url.URL {
+	t.Helper()
+
+	var err error
+	var rawURL string
+	require.Eventually(t, func() bool {
+		rawURL, err = cfg.URL().Read()
+		return err == nil && rawURL != ""
+	}, testutil.WaitLong, testutil.IntervalFast, "failed to get access URL")
+
+	accessURL, err := url.Parse(rawURL)
+	require.NoError(t, err, "failed to parse access URL")
+
+	return accessURL
+}
diff --git a/cli/ssh_test.go b/cli/ssh_test.go
index f88339c103fd9..6978e5da298ba 100644
--- a/cli/ssh_test.go
+++ b/cli/ssh_test.go
@@ -29,6 +29,7 @@ import (
 	"github.com/coder/coder/provisioner/echo"
 	"github.com/coder/coder/provisionersdk/proto"
 	"github.com/coder/coder/pty/ptytest"
+	"github.com/coder/coder/testutil"
 )
 
 func setupWorkspaceForSSH(t *testing.T) (*codersdk.Client, codersdk.Workspace, string) {
@@ -77,7 +78,7 @@ func TestSSH(t *testing.T) {
 		cmd.SetErr(pty.Output())
 		cmd.SetOut(pty.Output())
 
-		ctx, cancel := context.WithTimeout(context.Background(), 10*time.Second)
+		ctx, cancel := context.WithTimeout(context.Background(), testutil.WaitLong)
 		defer cancel()
 
 		cmdDone := tGo(t, func() {
@@ -124,7 +125,7 @@ func TestSSH(t *testing.T) {
 			}
 		}()
 
-		ctx, cancel := context.WithTimeout(context.Background(), 10*time.Second)
+		ctx, cancel := context.WithTimeout(context.Background(), testutil.WaitLong)
 		defer cancel()
 
 		cmd, root := clitest.New(t, "ssh", "--stdio", workspace.Name)
@@ -215,7 +216,7 @@ func TestSSH(t *testing.T) {
 			}
 		})
 
-		ctx, cancel := context.WithTimeout(context.Background(), 10*time.Second)
+		ctx, cancel := context.WithTimeout(context.Background(), testutil.WaitLong)
 		defer cancel()
 
 		cmd, root := clitest.New(t,
diff --git a/coderd/coderd_test.go b/coderd/coderd_test.go
index c457f729f8676..83c6155e14037 100644
--- a/coderd/coderd_test.go
+++ b/coderd/coderd_test.go
@@ -40,6 +40,7 @@ import (
 	"github.com/coder/coder/codersdk"
 	"github.com/coder/coder/provisioner/echo"
 	"github.com/coder/coder/provisionersdk/proto"
+	"github.com/coder/coder/testutil"
 )
 
 func TestMain(m *testing.M) {
@@ -157,7 +158,7 @@ func TestAuthorizeAllEndpoints(t *testing.T) {
 	require.Eventually(t, func() bool {
 		provisionerds, err := client.ProvisionerDaemons(ctx)
 		return assert.NoError(t, err) && len(provisionerds) > 0
-	}, time.Second*10, time.Second)
+	}, testutil.WaitLong, testutil.IntervalSlow)
 
 	provisionerds, err := client.ProvisionerDaemons(ctx)
 	require.NoError(t, err, "fetch provisioners")
diff --git a/coderd/coderdtest/coderdtest.go b/coderd/coderdtest/coderdtest.go
index c16f6f860dd11..6b0b2d425caaf 100644
--- a/coderd/coderdtest/coderdtest.go
+++ b/coderd/coderdtest/coderdtest.go
@@ -56,6 +56,7 @@ import (
 	"github.com/coder/coder/provisionerd"
 	"github.com/coder/coder/provisionersdk"
 	"github.com/coder/coder/provisionersdk/proto"
+	"github.com/coder/coder/testutil"
 )
 
 type Options struct {
@@ -180,7 +181,7 @@ func newWithCloser(t *testing.T, options *Options) (*codersdk.Client, io.Closer)
 		AgentConnectionUpdateFrequency: 150 * time.Millisecond,
 		// Force a long disconnection timeout to ensure
 		// agents are not marked as disconnected during slow tests.
-		AgentInactiveDisconnectTimeout: 5 * time.Second,
+		AgentInactiveDisconnectTimeout: testutil.WaitShort,
 		AccessURL:                      serverURL,
 		Logger:                         slogtest.Make(t, nil).Leveled(slog.LevelDebug),
 		CacheDir:                       t.TempDir(),
@@ -414,7 +415,7 @@ func AwaitTemplateVersionJob(t *testing.T, client *codersdk.Client, version uuid
 		var err error
 		templateVersion, err = client.TemplateVersion(context.Background(), version)
 		return assert.NoError(t, err) && templateVersion.Job.CompletedAt != nil
-	}, 5*time.Second, 25*time.Millisecond)
+	}, testutil.WaitShort, testutil.IntervalFast)
 	return templateVersion
 }
 
@@ -428,7 +429,7 @@ func AwaitWorkspaceBuildJob(t *testing.T, client *codersdk.Client, build uuid.UU
 		var err error
 		workspaceBuild, err = client.WorkspaceBuild(context.Background(), build)
 		return assert.NoError(t, err) && workspaceBuild.Job.CompletedAt != nil
-	}, 5*time.Second, 25*time.Millisecond)
+	}, testutil.WaitShort, testutil.IntervalFast)
 	return workspaceBuild
 }
 
@@ -452,7 +453,7 @@ func AwaitWorkspaceAgents(t *testing.T, client *codersdk.Client, build uuid.UUID
 			}
 		}
 		return true
-	}, 15*time.Second, 50*time.Millisecond)
+	}, testutil.WaitLong, testutil.IntervalMedium)
 	return resources
 }
 
diff --git a/coderd/devtunnel/tunnel_test.go b/coderd/devtunnel/tunnel_test.go
index 70007cc257191..23dd92d966d54 100644
--- a/coderd/devtunnel/tunnel_test.go
+++ b/coderd/devtunnel/tunnel_test.go
@@ -25,6 +25,7 @@ import (
 
 	"cdr.dev/slog/sloggers/slogtest"
 	"github.com/coder/coder/coderd/devtunnel"
+	"github.com/coder/coder/testutil"
 )
 
 const (
@@ -85,15 +86,15 @@ func TestTunnel(t *testing.T) {
 		_, _ = io.Copy(io.Discard, res.Body)
 
 		return res.StatusCode == http.StatusAccepted
-	}, time.Minute, time.Second)
+	}, testutil.WaitShort, testutil.IntervalSlow)
 
 	assert.NoError(t, server.Close())
 	cancelTun()
 
 	select {
 	case <-errCh:
-	case <-time.After(10 * time.Second):
-		t.Error("tunnel did not close after 10 seconds")
+	case <-time.After(testutil.WaitLong):
+		t.Errorf("tunnel did not close after %s", testutil.WaitLong)
 	}
 }
 
@@ -226,7 +227,7 @@ func (f *fakeTunnelServer) requestHTTP() (*http.Response, error) {
 	}
 	client := &http.Client{
 		Transport: transport,
-		Timeout:   10 * time.Second,
+		Timeout:   testutil.WaitLong,
 	}
 	return client.Get(fmt.Sprintf("http://[%s]:8090", clientIP))
 }
diff --git a/coderd/httpmw/ratelimit_test.go b/coderd/httpmw/ratelimit_test.go
index c2e4ebd41fd78..132615d669ab7 100644
--- a/coderd/httpmw/ratelimit_test.go
+++ b/coderd/httpmw/ratelimit_test.go
@@ -4,12 +4,12 @@ import (
 	"net/http"
 	"net/http/httptest"
 	"testing"
-	"time"
 
 	"github.com/go-chi/chi/v5"
 	"github.com/stretchr/testify/require"
 
 	"github.com/coder/coder/coderd/httpmw"
+	"github.com/coder/coder/testutil"
 )
 
 func TestRateLimit(t *testing.T) {
@@ -27,6 +27,6 @@ func TestRateLimit(t *testing.T) {
 			rec := httptest.NewRecorder()
 			rtr.ServeHTTP(rec, req)
 			return rec.Result().StatusCode == http.StatusTooManyRequests
-		}, 5*time.Second, time.Millisecond)
+		}, testutil.WaitShort, testutil.IntervalFast)
 	})
 }
diff --git a/coderd/provisionerdaemons_test.go b/coderd/provisionerdaemons_test.go
index 1a89bb4e701a8..709dc2eb0c092 100644
--- a/coderd/provisionerdaemons_test.go
+++ b/coderd/provisionerdaemons_test.go
@@ -5,7 +5,6 @@ import (
 	"crypto/rand"
 	"runtime"
 	"testing"
-	"time"
 
 	"github.com/stretchr/testify/assert"
 	"github.com/stretchr/testify/require"
@@ -13,6 +12,7 @@ import (
 	"github.com/coder/coder/coderd/coderdtest"
 	"github.com/coder/coder/codersdk"
 	"github.com/coder/coder/provisionersdk"
+	"github.com/coder/coder/testutil"
 )
 
 func TestProvisionerDaemons(t *testing.T) {
@@ -41,7 +41,7 @@ func TestProvisionerDaemons(t *testing.T) {
 			var err error
 			version, err = client.TemplateVersion(context.Background(), version.ID)
 			return assert.NoError(t, err) && version.Job.Error != ""
-		}, 5*time.Second, 25*time.Millisecond)
+		}, testutil.WaitShort, testutil.IntervalFast)
 	})
 }
 
diff --git a/coderd/provisionerjobs_internal_test.go b/coderd/provisionerjobs_internal_test.go
index 6a5cbcccfe5cd..4d215f6bb2a92 100644
--- a/coderd/provisionerjobs_internal_test.go
+++ b/coderd/provisionerjobs_internal_test.go
@@ -21,6 +21,7 @@ import (
 	"github.com/coder/coder/coderd/database"
 	"github.com/coder/coder/coderd/database/databasefake"
 	"github.com/coder/coder/codersdk"
+	"github.com/coder/coder/testutil"
 )
 
 func TestProvisionerJobLogs_Unit(t *testing.T) {
@@ -63,7 +64,7 @@ func TestProvisionerJobLogs_Unit(t *testing.T) {
 			{ID: uuid.New(), JobID: jobID, Stage: "Stage3"},
 		}
 
-		ctx, cancel := context.WithTimeout(context.Background(), 5*time.Second)
+		ctx, cancel := context.WithTimeout(context.Background(), testutil.WaitShort)
 		defer cancel()
 
 		// wow there are a lot of DB rows we touch...
diff --git a/coderd/templateversions_test.go b/coderd/templateversions_test.go
index 8706c77d25019..9c6c76a927fdd 100644
--- a/coderd/templateversions_test.go
+++ b/coderd/templateversions_test.go
@@ -14,6 +14,7 @@ import (
 	"github.com/coder/coder/codersdk"
 	"github.com/coder/coder/provisioner/echo"
 	"github.com/coder/coder/provisionersdk/proto"
+	"github.com/coder/coder/testutil"
 )
 
 func TestTemplateVersion(t *testing.T) {
@@ -120,7 +121,7 @@ func TestPatchCancelTemplateVersion(t *testing.T) {
 			}
 			t.Logf("Status: %s", version.Job.Status)
 			return version.Job.Status == codersdk.ProvisionerJobRunning
-		}, 5*time.Second, 25*time.Millisecond)
+		}, testutil.WaitShort, testutil.IntervalFast)
 		err := client.CancelTemplateVersion(context.Background(), version.ID)
 		require.NoError(t, err)
 		err = client.CancelTemplateVersion(context.Background(), version.ID)
@@ -131,7 +132,7 @@ func TestPatchCancelTemplateVersion(t *testing.T) {
 			var err error
 			version, err = client.TemplateVersion(context.Background(), version.ID)
 			return assert.NoError(t, err) && version.Job.Status == codersdk.ProvisionerJobFailed
-		}, 5*time.Second, 25*time.Millisecond)
+		}, testutil.WaitShort, testutil.IntervalFast)
 	})
 	// TODO(Cian): until we are able to test cancellation properly, validating
 	// Running -> Canceling is the best we can do for now.
@@ -155,7 +156,7 @@ func TestPatchCancelTemplateVersion(t *testing.T) {
 			}
 			t.Logf("Status: %s", version.Job.Status)
 			return version.Job.Status == codersdk.ProvisionerJobRunning
-		}, 5*time.Second, 25*time.Millisecond)
+		}, testutil.WaitShort, testutil.IntervalFast)
 		err := client.CancelTemplateVersion(context.Background(), version.ID)
 		require.NoError(t, err)
 		require.Eventually(t, func() bool {
@@ -166,7 +167,7 @@ func TestPatchCancelTemplateVersion(t *testing.T) {
 				// provision complete response.
 				assert.Empty(t, version.Job.Error) &&
 				version.Job.Status == codersdk.ProvisionerJobCanceling
-		}, 5*time.Second, 25*time.Millisecond)
+		}, testutil.WaitShort, testutil.IntervalFast)
 	})
 }
 
@@ -541,7 +542,7 @@ func TestTemplateVersionDryRun(t *testing.T) {
 		require.Eventually(t, func() bool {
 			job, err := client.TemplateVersionDryRun(ctx, version.ID, job.ID)
 			return assert.NoError(t, err) && job.Status == codersdk.ProvisionerJobSucceeded
-		}, 5*time.Second, 25*time.Millisecond)
+		}, testutil.WaitShort, testutil.IntervalFast)
 
 		<-logsDone
 
@@ -618,7 +619,7 @@ func TestTemplateVersionDryRun(t *testing.T) {
 
 				t.Logf("Status: %s", job.Status)
 				return job.Status == codersdk.ProvisionerJobPending
-			}, 5*time.Second, 25*time.Millisecond)
+			}, testutil.WaitShort, testutil.IntervalFast)
 
 			err = client.CancelTemplateVersionDryRun(context.Background(), version.ID, job.ID)
 			require.NoError(t, err)
@@ -631,7 +632,7 @@ func TestTemplateVersionDryRun(t *testing.T) {
 
 				t.Logf("Status: %s", job.Status)
 				return job.Status == codersdk.ProvisionerJobCanceling
-			}, 5*time.Second, 25*time.Millisecond)
+			}, testutil.WaitShort, testutil.IntervalFast)
 		})
 
 		t.Run("AlreadyCompleted", func(t *testing.T) {
@@ -655,7 +656,7 @@ func TestTemplateVersionDryRun(t *testing.T) {
 
 				t.Logf("Status: %s", job.Status)
 				return job.Status == codersdk.ProvisionerJobSucceeded
-			}, 5*time.Second, 25*time.Millisecond)
+			}, testutil.WaitShort, testutil.IntervalFast)
 
 			err = client.CancelTemplateVersionDryRun(context.Background(), version.ID, job.ID)
 			var apiErr *codersdk.Error
diff --git a/coderd/workspacebuilds_test.go b/coderd/workspacebuilds_test.go
index 56f705940a72b..8b68cff559c94 100644
--- a/coderd/workspacebuilds_test.go
+++ b/coderd/workspacebuilds_test.go
@@ -17,6 +17,7 @@ import (
 	"github.com/coder/coder/codersdk"
 	"github.com/coder/coder/provisioner/echo"
 	"github.com/coder/coder/provisionersdk/proto"
+	"github.com/coder/coder/testutil"
 )
 
 func TestWorkspaceBuild(t *testing.T) {
@@ -222,7 +223,7 @@ func TestPatchCancelWorkspaceBuild(t *testing.T) {
 		var err error
 		build, err = client.WorkspaceBuild(context.Background(), workspace.LatestBuild.ID)
 		return assert.NoError(t, err) && build.Job.Status == codersdk.ProvisionerJobRunning
-	}, 5*time.Second, 25*time.Millisecond)
+	}, testutil.WaitShort, testutil.IntervalFast)
 	err := client.CancelWorkspaceBuild(context.Background(), build.ID)
 	require.NoError(t, err)
 	require.Eventually(t, func() bool {
@@ -233,7 +234,7 @@ func TestPatchCancelWorkspaceBuild(t *testing.T) {
 			// provision complete response.
 			assert.Empty(t, build.Job.Error) &&
 			build.Job.Status == codersdk.ProvisionerJobCanceling
-	}, 5*time.Second, 25*time.Millisecond)
+	}, testutil.WaitShort, testutil.IntervalFast)
 }
 
 func TestWorkspaceBuildResources(t *testing.T) {
diff --git a/peer/conn_test.go b/peer/conn_test.go
index d1fbf63d15ab6..6e2de345f0d9e 100644
--- a/peer/conn_test.go
+++ b/peer/conn_test.go
@@ -21,6 +21,7 @@ import (
 	"cdr.dev/slog"
 	"cdr.dev/slog/sloggers/slogtest"
 	"github.com/coder/coder/peer"
+	"github.com/coder/coder/testutil"
 )
 
 var (
@@ -109,7 +110,7 @@ func TestConn(t *testing.T) {
 		t.Parallel()
 		client, server, _ := createPair(t)
 		exchange(t, client, server)
-		ctx, cancel := context.WithTimeout(context.Background(), 15*time.Second)
+		ctx, cancel := context.WithTimeout(context.Background(), testutil.WaitLong)
 		defer cancel()
 		cch, err := client.CreateChannel(ctx, "hello", &peer.ChannelOptions{})
 		require.NoError(t, err)
@@ -128,7 +129,7 @@ func TestConn(t *testing.T) {
 		t.Parallel()
 		client, server, wan := createPair(t)
 		exchange(t, client, server)
-		ctx, cancel := context.WithTimeout(context.Background(), 15*time.Second)
+		ctx, cancel := context.WithTimeout(context.Background(), testutil.WaitLong)
 		defer cancel()
 		cch, err := client.CreateChannel(ctx, "hello", &peer.ChannelOptions{})
 		require.NoError(t, err)
@@ -148,7 +149,7 @@ func TestConn(t *testing.T) {
 		t.Parallel()
 		client, server, _ := createPair(t)
 		exchange(t, client, server)
-		ctx, cancel := context.WithTimeout(context.Background(), 15*time.Second)
+		ctx, cancel := context.WithTimeout(context.Background(), testutil.WaitLong)
 		defer cancel()
 		cch, err := client.CreateChannel(ctx, "hello", &peer.ChannelOptions{})
 		require.NoError(t, err)
@@ -196,7 +197,7 @@ func TestConn(t *testing.T) {
 		srv, err := net.Listen("tcp", "127.0.0.1:0")
 		require.NoError(t, err)
 		defer srv.Close()
-		ctx, cancel := context.WithTimeout(context.Background(), 15*time.Second)
+		ctx, cancel := context.WithTimeout(context.Background(), testutil.WaitLong)
 		defer cancel()
 		go func() {
 			sch, err := server.Accept(ctx)
@@ -314,7 +315,7 @@ func TestConn(t *testing.T) {
 		t.Parallel()
 		client, server, _ := createPair(t)
 		exchange(t, client, server)
-		ctx, cancel := context.WithTimeout(context.Background(), 15*time.Second)
+		ctx, cancel := context.WithTimeout(context.Background(), testutil.WaitLong)
 		defer cancel()
 		go func() {
 			channel, err := client.CreateChannel(ctx, "test", nil)
diff --git a/provisionerd/provisionerd_test.go b/provisionerd/provisionerd_test.go
index fd724babea853..05becb863ebd7 100644
--- a/provisionerd/provisionerd_test.go
+++ b/provisionerd/provisionerd_test.go
@@ -13,6 +13,7 @@ import (
 	"time"
 
 	"github.com/coder/coder/provisionerd/runner"
+	"github.com/coder/coder/testutil"
 
 	"github.com/hashicorp/yamux"
 	"github.com/stretchr/testify/assert"
@@ -69,7 +70,7 @@ func TestProvisionerd(t *testing.T) {
 			defer close(completeChan)
 			return nil, xerrors.New("an error")
 		}, provisionerd.Provisioners{})
-		require.Condition(t, closedWithin(completeChan, 5*time.Second))
+		require.Condition(t, closedWithin(completeChan, testutil.WaitShort))
 		require.NoError(t, closer.Close())
 	})
 
@@ -92,7 +93,7 @@ func TestProvisionerd(t *testing.T) {
 				updateJob: noopUpdateJob,
 			}), nil
 		}, provisionerd.Provisioners{})
-		require.Condition(t, closedWithin(completeChan, 5*time.Second))
+		require.Condition(t, closedWithin(completeChan, testutil.WaitShort))
 		require.NoError(t, closer.Close())
 	})
 
@@ -137,7 +138,7 @@ func TestProvisionerd(t *testing.T) {
 			}),
 		})
 		closerMutex.Unlock()
-		require.Condition(t, closedWithin(completeChan, 5*time.Second))
+		require.Condition(t, closedWithin(completeChan, testutil.WaitShort))
 		require.NoError(t, closer.Close())
 	})
 
@@ -175,7 +176,7 @@ func TestProvisionerd(t *testing.T) {
 		}, provisionerd.Provisioners{
 			"someprovisioner": createProvisionerClient(t, provisionerTestServer{}),
 		})
-		require.Condition(t, closedWithin(completeChan, 5*time.Second))
+		require.Condition(t, closedWithin(completeChan, testutil.WaitShort))
 		require.NoError(t, closer.Close())
 	})
 
@@ -218,7 +219,7 @@ func TestProvisionerd(t *testing.T) {
 				},
 			}),
 		})
-		require.Condition(t, closedWithin(completeChan, 5*time.Second))
+		require.Condition(t, closedWithin(completeChan, testutil.WaitShort))
 		require.NoError(t, closer.Close())
 	})
 
@@ -323,7 +324,7 @@ func TestProvisionerd(t *testing.T) {
 				},
 			}),
 		})
-		require.Condition(t, closedWithin(completeChan, 5*time.Second))
+		require.Condition(t, closedWithin(completeChan, testutil.WaitShort))
 		require.True(t, didLog.Load())
 		require.True(t, didComplete.Load())
 		require.True(t, didDryRun.Load())
@@ -403,7 +404,7 @@ func TestProvisionerd(t *testing.T) {
 			}),
 		})
 
-		require.Condition(t, closedWithin(completeChan, 5*time.Second))
+		require.Condition(t, closedWithin(completeChan, testutil.WaitShort))
 		require.True(t, didLog.Load())
 		require.True(t, didComplete.Load())
 		require.NoError(t, closer.Close())
@@ -474,7 +475,7 @@ func TestProvisionerd(t *testing.T) {
 				},
 			}),
 		})
-		require.Condition(t, closedWithin(completeChan, 5*time.Second))
+		require.Condition(t, closedWithin(completeChan, testutil.WaitShort))
 		require.True(t, didLog.Load())
 		require.True(t, didComplete.Load())
 		require.NoError(t, closer.Close())
@@ -529,7 +530,7 @@ func TestProvisionerd(t *testing.T) {
 				},
 			}),
 		})
-		require.Condition(t, closedWithin(completeChan, 5*time.Second))
+		require.Condition(t, closedWithin(completeChan, testutil.WaitShort))
 		require.True(t, didFail.Load())
 		require.NoError(t, closer.Close())
 	})
@@ -602,10 +603,10 @@ func TestProvisionerd(t *testing.T) {
 				},
 			}),
 		})
-		require.Condition(t, closedWithin(updateChan, 5*time.Second))
+		require.Condition(t, closedWithin(updateChan, testutil.WaitShort))
 		err := server.Shutdown(context.Background())
 		require.NoError(t, err)
-		require.Condition(t, closedWithin(completeChan, 5*time.Second))
+		require.Condition(t, closedWithin(completeChan, testutil.WaitShort))
 		require.NoError(t, server.Close())
 	})
 
@@ -685,8 +686,8 @@ func TestProvisionerd(t *testing.T) {
 				},
 			}),
 		})
-		require.Condition(t, closedWithin(updateChan, 5*time.Second))
-		require.Condition(t, closedWithin(completeChan, 5*time.Second))
+		require.Condition(t, closedWithin(updateChan, testutil.WaitShort))
+		require.Condition(t, closedWithin(completeChan, testutil.WaitShort))
 		require.NoError(t, server.Close())
 	})
 
@@ -758,7 +759,7 @@ func TestProvisionerd(t *testing.T) {
 				},
 			}),
 		})
-		require.Condition(t, closedWithin(completeChan, 5*time.Second))
+		require.Condition(t, closedWithin(completeChan, testutil.WaitShort))
 		require.NoError(t, server.Close())
 	})
 
@@ -830,7 +831,7 @@ func TestProvisionerd(t *testing.T) {
 				},
 			}),
 		})
-		require.Condition(t, closedWithin(completeChan, 5*time.Second))
+		require.Condition(t, closedWithin(completeChan, testutil.WaitShort))
 		require.NoError(t, server.Close())
 	})
 
@@ -915,7 +916,7 @@ func TestProvisionerd(t *testing.T) {
 				},
 			}),
 		})
-		require.Condition(t, closedWithin(completeChan, 5*time.Second))
+		require.Condition(t, closedWithin(completeChan, testutil.WaitShort))
 		m.Lock()
 		defer m.Unlock()
 		require.Equal(t, ops[len(ops)-1], "CompleteJob")
diff --git a/pty/ptytest/ptytest.go b/pty/ptytest/ptytest.go
index dc22351416c50..2c79ae1991d1d 100644
--- a/pty/ptytest/ptytest.go
+++ b/pty/ptytest/ptytest.go
@@ -17,6 +17,7 @@ import (
 	"golang.org/x/xerrors"
 
 	"github.com/coder/coder/pty"
+	"github.com/coder/coder/testutil"
 )
 
 func New(t *testing.T) *PTY {
@@ -85,7 +86,7 @@ type PTY struct {
 func (p *PTY) ExpectMatch(str string) string {
 	p.t.Helper()
 
-	timeout, cancel := context.WithTimeout(context.Background(), 10*time.Second)
+	timeout, cancel := context.WithTimeout(context.Background(), testutil.WaitMedium)
 	defer cancel()
 
 	var buffer bytes.Buffer
diff --git a/scripts/rules.go b/scripts/rules.go
index 16917101d16e9..d77289388ba1c 100644
--- a/scripts/rules.go
+++ b/scripts/rules.go
@@ -81,6 +81,43 @@ func doNotCallTFailNowInsideGoroutine(m dsl.Matcher) {
 		Report("Do not call functions that may call t.FailNow in a goroutine, as this can cause data races (see testing.go:834)")
 }
 
+// useStandardTimeoutsAndDelaysInTests ensures all tests use common
+// constants for timeouts and delays in usual scenarios, this allows us
+// to tweak them based on platform (important to avoid CI flakes).
+//nolint:unused,deadcode,varnamelen
+func useStandardTimeoutsAndDelaysInTests(m dsl.Matcher) {
+	m.Import("github.com/stretchr/testify/require")
+	m.Import("github.com/stretchr/testify/assert")
+	m.Import("github.com/coder/coder/testutil")
+
+	m.Match(`context.WithTimeout($ctx, $duration)`).
+		Where(m.File().Imports("testing") && !m["duration"].Text.Matches("^testutil\\.")).
+		At(m["duration"]).
+		Report("Do not use magic numbers in test timeouts and delays. Use the standard testutil.Wait* or testutil.Interval* constants instead.")
+
+	m.Match(`
+		$testify.$Eventually($t, func() bool {
+			$*_
+		}, $timeout, $interval, $*_)
+	`).
+		Where((m["testify"].Text == "require" || m["testify"].Text == "assert") &&
+			(m["Eventually"].Text == "Eventually" || m["Eventually"].Text == "Eventuallyf") &&
+			!m["timeout"].Text.Matches("^testutil\\.")).
+		At(m["timeout"]).
+		Report("Do not use magic numbers in test timeouts and delays. Use the standard testutil.Wait* or testutil.Interval* constants instead.")
+
+	m.Match(`
+		$testify.$Eventually($t, func() bool {
+			$*_
+		}, $timeout, $interval, $*_)
+	`).
+		Where((m["testify"].Text == "require" || m["testify"].Text == "assert") &&
+			(m["Eventually"].Text == "Eventually" || m["Eventually"].Text == "Eventuallyf") &&
+			!m["interval"].Text.Matches("^testutil\\.")).
+		At(m["interval"]).
+		Report("Do not use magic numbers in test timeouts and delays. Use the standard testutil.Wait* or testutil.Interval* constants instead.")
+}
+
 // InTx checks to ensure the database used inside the transaction closure is the transaction
 // database, and not the original database that creates the tx.
 func InTx(m dsl.Matcher) {
diff --git a/site/site_test.go b/site/site_test.go
index 27b6edcbbf527..7b28ac91b3a6a 100644
--- a/site/site_test.go
+++ b/site/site_test.go
@@ -20,6 +20,7 @@ import (
 	"github.com/stretchr/testify/require"
 
 	"github.com/coder/coder/site"
+	"github.com/coder/coder/testutil"
 )
 
 func TestCaching(t *testing.T) {
@@ -48,7 +49,7 @@ func TestCaching(t *testing.T) {
 	defer srv.Close()
 
 	// Create a context
-	ctx, cancelFunc := context.WithTimeout(context.Background(), 5*time.Second)
+	ctx, cancelFunc := context.WithTimeout(context.Background(), testutil.WaitShort)
 	defer cancelFunc()
 
 	testCases := []struct {
@@ -108,7 +109,7 @@ func TestServingFiles(t *testing.T) {
 	defer srv.Close()
 
 	// Create a context
-	ctx, cancelFunc := context.WithTimeout(context.Background(), 5*time.Second)
+	ctx, cancelFunc := context.WithTimeout(context.Background(), testutil.WaitShort)
 	defer cancelFunc()
 
 	testCases := []struct {
@@ -337,7 +338,7 @@ func TestServingBin(t *testing.T) {
 			defer srv.Close()
 
 			// Create a context
-			ctx, cancelFunc := context.WithTimeout(context.Background(), 5*time.Second)
+			ctx, cancelFunc := context.WithTimeout(context.Background(), testutil.WaitShort)
 			defer cancelFunc()
 
 			for _, tr := range tt.reqs {
diff --git a/testutil/duration.go b/testutil/duration.go
new file mode 100644
index 0000000000000..8e3210f155178
--- /dev/null
+++ b/testutil/duration.go
@@ -0,0 +1,21 @@
+//go:build !windows
+
+package testutil
+
+import "time"
+
+// Constants for timing out operations, usable for creating contexts
+// that timeout or in require.Eventually.
+const (
+	WaitShort  = 5 * time.Second
+	WaitMedium = 10 * time.Second
+	WaitLong   = 15 * time.Second
+)
+
+// Constants for delaying repeated operations, e.g. in
+// require.Eventually.
+const (
+	IntervalFast   = 25 * time.Millisecond
+	IntervalMedium = 250 * time.Millisecond
+	IntervalSlow   = time.Second
+)
diff --git a/testutil/duration_windows.go b/testutil/duration_windows.go
new file mode 100644
index 0000000000000..5707824800bbf
--- /dev/null
+++ b/testutil/duration_windows.go
@@ -0,0 +1,23 @@
+package testutil
+
+import "time"
+
+// Constants for timing out operations, usable for creating contexts
+// that timeout or in require.Eventually.
+//
+// Windows durations are adjusted for slow CI workers.
+const (
+	WaitShort  = 10 * time.Second
+	WaitMedium = 20 * time.Second
+	WaitLong   = 30 * time.Second
+)
+
+// Constants for delaying repeated operations, e.g. in
+// require.Eventually.
+//
+// Windows durations are adjusted for slow CI workers.
+const (
+	IntervalFast   = 50 * time.Millisecond
+	IntervalMedium = 500 * time.Millisecond
+	IntervalSlow   = 2 * time.Second
+)