diff --git a/cli/agent.go b/cli/agent.go
index fa62761cc1716..0cdfc66c80323 100644
--- a/cli/agent.go
+++ b/cli/agent.go
@@ -116,7 +116,7 @@ func (r *RootCmd) workspaceAgent() *clibase.Cmd {
 				defer logWriter.Close()
 
 				sinks = append(sinks, sloghuman.Sink(logWriter))
-				logger := slog.Make(sinks...).Leveled(slog.LevelDebug)
+				logger := inv.Logger.AppendSinks(sinks...).Leveled(slog.LevelDebug)
 
 				logger.Info(ctx, "spawning reaper process")
 				// Do not start a reaper on the child process. It's important
@@ -159,7 +159,7 @@ func (r *RootCmd) workspaceAgent() *clibase.Cmd {
 			defer logWriter.Close()
 
 			sinks = append(sinks, sloghuman.Sink(logWriter))
-			logger := slog.Make(sinks...).Leveled(slog.LevelDebug)
+			logger := inv.Logger.AppendSinks(sinks...).Leveled(slog.LevelDebug)
 
 			version := buildinfo.Version()
 			logger.Info(ctx, "agent is starting now",
diff --git a/cli/agent_test.go b/cli/agent_test.go
index a1f519cf4dada..1f366da8b4ced 100644
--- a/cli/agent_test.go
+++ b/cli/agent_test.go
@@ -20,7 +20,7 @@ import (
 	"github.com/coder/coder/v2/coderd/database/dbfake"
 	"github.com/coder/coder/v2/codersdk"
 	"github.com/coder/coder/v2/provisionersdk/proto"
-	"github.com/coder/coder/v2/pty/ptytest"
+	"github.com/coder/coder/v2/testutil"
 )
 
 func TestWorkspaceAgent(t *testing.T) {
@@ -44,17 +44,17 @@ func TestWorkspaceAgent(t *testing.T) {
 			"--log-dir", logDir,
 		)
 
-		pty := ptytest.New(t).Attach(inv)
-
 		clitest.Start(t, inv)
-		ctx := inv.Context()
-		pty.ExpectMatchContext(ctx, "agent is starting now")
 
 		coderdtest.AwaitWorkspaceAgents(t, client, ws.ID)
 
-		info, err := os.Stat(filepath.Join(logDir, "coder-agent.log"))
-		require.NoError(t, err)
-		require.Greater(t, info.Size(), int64(0))
+		require.Eventually(t, func() bool {
+			info, err := os.Stat(filepath.Join(logDir, "coder-agent.log"))
+			if err != nil {
+				return false
+			}
+			return info.Size() > 0
+		}, testutil.WaitLong, testutil.IntervalMedium)
 	})
 
 	t.Run("Azure", func(t *testing.T) {
@@ -84,6 +84,7 @@ func TestWorkspaceAgent(t *testing.T) {
 			//nolint:revive,staticcheck
 			context.WithValue(inv.Context(), "azure-client", metadataClient),
 		)
+
 		ctx := inv.Context()
 		clitest.Start(t, inv)
 		coderdtest.AwaitWorkspaceAgents(t, client, ws.ID)
@@ -126,6 +127,7 @@ func TestWorkspaceAgent(t *testing.T) {
 			//nolint:revive,staticcheck
 			context.WithValue(inv.Context(), "aws-client", metadataClient),
 		)
+
 		clitest.Start(t, inv)
 		ctx := inv.Context()
 		coderdtest.AwaitWorkspaceAgents(t, client, ws.ID)
@@ -164,8 +166,8 @@ func TestWorkspaceAgent(t *testing.T) {
 			}},
 		})
 		inv, cfg := clitest.New(t, "agent", "--auth", "google-instance-identity", "--agent-url", client.URL.String())
-		ptytest.New(t).Attach(inv)
 		clitest.SetupConfig(t, member, cfg)
+
 		clitest.Start(t,
 			inv.WithContext(
 				//nolint:revive,staticcheck
@@ -223,10 +225,7 @@ func TestWorkspaceAgent(t *testing.T) {
 		// Set the subsystems for the agent.
 		inv.Environ.Set(agent.EnvAgentSubsystem, fmt.Sprintf("%s,%s", codersdk.AgentSubsystemExectrace, codersdk.AgentSubsystemEnvbox))
 
-		pty := ptytest.New(t).Attach(inv)
-
 		clitest.Start(t, inv)
-		pty.ExpectMatchContext(inv.Context(), "agent is starting now")
 
 		resources := coderdtest.AwaitWorkspaceAgents(t, client, ws.ID)
 		require.Len(t, resources, 1)
diff --git a/cli/clibase/cmd.go b/cli/clibase/cmd.go
index a2ca36b2c9142..d6789108870f3 100644
--- a/cli/clibase/cmd.go
+++ b/cli/clibase/cmd.go
@@ -12,6 +12,8 @@ import (
 	"testing"
 	"unicode"
 
+	"cdr.dev/slog"
+
 	"github.com/spf13/pflag"
 	"golang.org/x/exp/slices"
 	"golang.org/x/xerrors"
@@ -170,6 +172,7 @@ func (c *Cmd) Invoke(args ...string) *Invocation {
 		Stdout:  io.Discard,
 		Stderr:  io.Discard,
 		Stdin:   strings.NewReader(""),
+		Logger:  slog.Make(),
 	}
 }
 
@@ -185,6 +188,7 @@ type Invocation struct {
 	Stdout  io.Writer
 	Stderr  io.Writer
 	Stdin   io.Reader
+	Logger  slog.Logger
 
 	// testing
 	signalNotifyContext func(parent context.Context, signals ...os.Signal) (ctx context.Context, stop context.CancelFunc)
diff --git a/cli/clitest/clitest.go b/cli/clitest/clitest.go
index 23acc7c01b9d3..451757debf3e1 100644
--- a/cli/clitest/clitest.go
+++ b/cli/clitest/clitest.go
@@ -59,13 +59,18 @@ func NewWithCommand(
 	t testing.TB, cmd *clibase.Cmd, args ...string,
 ) (*clibase.Invocation, config.Root) {
 	configDir := config.Root(t.TempDir())
-	logger := slogtest.Make(t, nil)
+	// I really would like to fail test on error logs, but realistically, turning on by default
+	// in all our CLI tests is going to create a lot of flaky noise.
+	logger := slogtest.Make(t, &slogtest.Options{IgnoreErrors: true}).
+		Leveled(slog.LevelDebug).
+		Named("cli")
 	i := &clibase.Invocation{
 		Command: cmd,
 		Args:    append([]string{"--global-config", string(configDir)}, args...),
 		Stdin:   io.LimitReader(nil, 0),
 		Stdout:  (&logWriter{prefix: "stdout", log: logger}),
 		Stderr:  (&logWriter{prefix: "stderr", log: logger}),
+		Logger:  logger,
 	}
 	t.Logf("invoking command: %s %s", cmd.Name(), strings.Join(i.Args, " "))
 
diff --git a/cli/exp_scaletest.go b/cli/exp_scaletest.go
index 32f3bdd47e062..748fcdb6dc345 100644
--- a/cli/exp_scaletest.go
+++ b/cli/exp_scaletest.go
@@ -882,7 +882,7 @@ func (r *RootCmd) scaletestWorkspaceTraffic() *clibase.Cmd {
 			reg := prometheus.NewRegistry()
 			metrics := workspacetraffic.NewMetrics(reg, "username", "workspace_name", "agent_name")
 
-			logger := slog.Make(sloghuman.Sink(io.Discard))
+			logger := inv.Logger
 			prometheusSrvClose := ServeHandler(ctx, logger, promhttp.HandlerFor(reg, promhttp.HandlerOpts{}), prometheusFlags.Address, "prometheus")
 			defer prometheusSrvClose()
 
@@ -1075,7 +1075,7 @@ func (r *RootCmd) scaletestDashboard() *clibase.Cmd {
 				return xerrors.Errorf("--jitter must be less than --interval")
 			}
 			ctx := inv.Context()
-			logger := slog.Make(sloghuman.Sink(inv.Stdout)).Leveled(slog.LevelInfo)
+			logger := inv.Logger.AppendSinks(sloghuman.Sink(inv.Stdout))
 			if r.verbose {
 				logger = logger.Leveled(slog.LevelDebug)
 			}
diff --git a/cli/ping.go b/cli/ping.go
index 2df0d57446780..94ca23e3aa459 100644
--- a/cli/ping.go
+++ b/cli/ping.go
@@ -46,9 +46,9 @@ func (r *RootCmd) ping() *clibase.Cmd {
 				return err
 			}
 
-			var logger slog.Logger
+			logger := inv.Logger
 			if r.verbose {
-				logger = slog.Make(sloghuman.Sink(inv.Stdout)).Leveled(slog.LevelDebug)
+				logger = logger.AppendSinks(sloghuman.Sink(inv.Stdout)).Leveled(slog.LevelDebug)
 			}
 
 			if r.disableDirect {
diff --git a/cli/portforward.go b/cli/portforward.go
index d47a6acb2280c..73a279200cd5d 100644
--- a/cli/portforward.go
+++ b/cli/portforward.go
@@ -98,9 +98,9 @@ func (r *RootCmd) portForward() *clibase.Cmd {
 				return xerrors.Errorf("await agent: %w", err)
 			}
 
-			logger := slog.Make()
+			logger := inv.Logger
 			if r.verbose {
-				logger = slog.Make(sloghuman.Sink(inv.Stdout)).Leveled(slog.LevelDebug)
+				logger = logger.AppendSinks(sloghuman.Sink(inv.Stdout)).Leveled(slog.LevelDebug)
 			}
 
 			if r.disableDirect {
diff --git a/cli/root.go b/cli/root.go
index ecb5e1309a11a..8d645ea5f1d7a 100644
--- a/cli/root.go
+++ b/cli/root.go
@@ -30,7 +30,6 @@ import (
 
 	"github.com/coder/pretty"
 
-	"cdr.dev/slog"
 	"github.com/coder/coder/v2/buildinfo"
 	"github.com/coder/coder/v2/cli/clibase"
 	"github.com/coder/coder/v2/cli/cliui"
@@ -442,21 +441,6 @@ func (r *RootCmd) Command(subcommands []*clibase.Cmd) (*clibase.Cmd, error) {
 	return cmd, nil
 }
 
-type contextKey int
-
-const (
-	contextKeyLogger contextKey = iota
-)
-
-func ContextWithLogger(ctx context.Context, l slog.Logger) context.Context {
-	return context.WithValue(ctx, contextKeyLogger, l)
-}
-
-func LoggerFromContext(ctx context.Context) (slog.Logger, bool) {
-	l, ok := ctx.Value(contextKeyLogger).(slog.Logger)
-	return l, ok
-}
-
 // RootCmd contains parameters and helpers useful to all commands.
 type RootCmd struct {
 	clientURL      *url.URL
diff --git a/cli/server.go b/cli/server.go
index b09f814068343..ab2f7bb01e892 100644
--- a/cli/server.go
+++ b/cli/server.go
@@ -1092,7 +1092,7 @@ func (r *RootCmd) Server(newAPI func(context.Context, *coderd.Options) (*coderd.
 			ctx := inv.Context()
 
 			cfg := r.createConfig()
-			logger := slog.Make(sloghuman.Sink(inv.Stderr))
+			logger := inv.Logger.AppendSinks(sloghuman.Sink(inv.Stderr))
 			if ok, _ := inv.ParsedFlags().GetBool(varVerbose); ok {
 				logger = logger.Leveled(slog.LevelDebug)
 			}
@@ -2063,7 +2063,7 @@ func BuildLogger(inv *clibase.Invocation, cfg *codersdk.DeploymentValues) (slog.
 		level = slog.LevelDebug
 	}
 
-	return slog.Make(filter).Leveled(level), func() {
+	return inv.Logger.AppendSinks(filter).Leveled(level), func() {
 		for _, closer := range closers {
 			_ = closer()
 		}
diff --git a/cli/server_createadminuser.go b/cli/server_createadminuser.go
index 3200177b6dc54..7491afac3c3f8 100644
--- a/cli/server_createadminuser.go
+++ b/cli/server_createadminuser.go
@@ -42,7 +42,7 @@ func (r *RootCmd) newCreateAdminUserCommand() *clibase.Cmd {
 			}
 
 			cfg := r.createConfig()
-			logger := slog.Make(sloghuman.Sink(inv.Stderr))
+			logger := inv.Logger.AppendSinks(sloghuman.Sink(inv.Stderr))
 			if r.verbose {
 				logger = logger.Leveled(slog.LevelDebug)
 			}
diff --git a/cli/speedtest.go b/cli/speedtest.go
index ca6c5e50a6f05..bfc259dc67eda 100644
--- a/cli/speedtest.go
+++ b/cli/speedtest.go
@@ -48,10 +48,7 @@ func (r *RootCmd) speedtest() *clibase.Cmd {
 				return xerrors.Errorf("await agent: %w", err)
 			}
 
-			logger, ok := LoggerFromContext(ctx)
-			if !ok {
-				logger = slog.Make(sloghuman.Sink(inv.Stderr))
-			}
+			logger := inv.Logger.AppendSinks(sloghuman.Sink(inv.Stderr))
 			if r.verbose {
 				logger = logger.Leveled(slog.LevelDebug)
 			}
diff --git a/cli/speedtest_test.go b/cli/speedtest_test.go
index f16b769cc85e7..66dcab5abbeae 100644
--- a/cli/speedtest_test.go
+++ b/cli/speedtest_test.go
@@ -10,7 +10,6 @@ import (
 	"cdr.dev/slog"
 	"cdr.dev/slog/sloggers/slogtest"
 	"github.com/coder/coder/v2/agent/agenttest"
-	"github.com/coder/coder/v2/cli"
 	"github.com/coder/coder/v2/cli/clitest"
 	"github.com/coder/coder/v2/coderd/coderdtest"
 	"github.com/coder/coder/v2/codersdk"
@@ -50,7 +49,7 @@ func TestSpeedtest(t *testing.T) {
 	ctx, cancel = context.WithTimeout(context.Background(), testutil.WaitLong)
 	defer cancel()
 
-	ctx = cli.ContextWithLogger(ctx, slogtest.Make(t, nil).Named("speedtest").Leveled(slog.LevelDebug))
+	inv.Logger = slogtest.Make(t, nil).Named("speedtest").Leveled(slog.LevelDebug)
 	cmdDone := tGo(t, func() {
 		err := inv.WithContext(ctx).Run()
 		assert.NoError(t, err)
diff --git a/cli/ssh.go b/cli/ssh.go
index 9287ee1ef13c0..0b0a81f2ad83e 100644
--- a/cli/ssh.go
+++ b/cli/ssh.go
@@ -74,7 +74,7 @@ func (r *RootCmd) ssh() *clibase.Cmd {
 			ctx, cancel := context.WithCancel(ctx)
 			defer cancel()
 
-			logger := slog.Make() // empty logger
+			logger := inv.Logger
 			defer func() {
 				if retErr != nil {
 					// catch and log all returned errors so we see them in the
diff --git a/cli/ssh_test.go b/cli/ssh_test.go
index 77eae7d3b05fa..0f94fcce90ebd 100644
--- a/cli/ssh_test.go
+++ b/cli/ssh_test.go
@@ -215,6 +215,7 @@ func TestSSH(t *testing.T) {
 		inv.Stdin = clientOutput
 		inv.Stdout = serverInput
 		inv.Stderr = io.Discard
+
 		cmdDone := tGo(t, func() {
 			err := inv.WithContext(ctx).Run()
 			assert.NoError(t, err)
@@ -390,6 +391,7 @@ func TestSSH(t *testing.T) {
 		inv.Stdin = clientOutput
 		inv.Stdout = serverInput
 		inv.Stderr = io.Discard
+
 		cmdDone := tGo(t, func() {
 			err := inv.WithContext(ctx).Run()
 			assert.NoError(t, err)
diff --git a/cli/vscodessh.go b/cli/vscodessh.go
index 87458d85833af..5a61946cdad3d 100644
--- a/cli/vscodessh.go
+++ b/cli/vscodessh.go
@@ -138,7 +138,7 @@ func (r *RootCmd) vscodeSSH() *clibase.Cmd {
 			// command via the ProxyCommand SSH option.
 			pid := os.Getppid()
 
-			logger := slog.Make()
+			logger := inv.Logger
 			if logDir != "" {
 				logFilePath := filepath.Join(logDir, fmt.Sprintf("%d.log", pid))
 				logFile, err := fs.OpenFile(logFilePath, os.O_CREATE|os.O_WRONLY, 0o600)