diff --git a/agent/agent.go b/agent/agent.go
index 5ca733f2f5464..53fafe831e30b 100644
--- a/agent/agent.go
+++ b/agent/agent.go
@@ -12,6 +12,7 @@ import (
 	"os"
 	"os/exec"
 	"os/user"
+	"path/filepath"
 	"runtime"
 	"strconv"
 	"strings"
@@ -21,7 +22,6 @@ import (
 	"github.com/armon/circbuf"
 	"github.com/google/uuid"
 
-	gsyslog "github.com/hashicorp/go-syslog"
 	"go.uber.org/atomic"
 
 	"cdr.dev/slog"
@@ -166,15 +166,9 @@ func (*agent) runStartupScript(ctx context.Context, script string) error {
 		return xerrors.Errorf("get user shell: %w", err)
 	}
 
-	var writer io.WriteCloser
-	// Attempt to use the syslog to write startup information.
-	writer, err = gsyslog.NewLogger(gsyslog.LOG_INFO, "USER", "coder-startup-script")
+	writer, err := os.OpenFile(filepath.Join(os.TempDir(), "coder-startup-script.log"), os.O_CREATE|os.O_RDWR, 0600)
 	if err != nil {
-		// If the syslog isn't supported or cannot be created, use a text file in temp.
-		writer, err = os.CreateTemp("", "coder-startup-script-*.txt")
-		if err != nil {
-			return xerrors.Errorf("open startup script log file: %w", err)
-		}
+		return xerrors.Errorf("open startup script log file: %w", err)
 	}
 	defer func() {
 		_ = writer.Close()
diff --git a/cli/agent.go b/cli/agent.go
index e9220840387e8..238a1e858923b 100644
--- a/cli/agent.go
+++ b/cli/agent.go
@@ -4,6 +4,8 @@ import (
 	"context"
 	"net/http"
 	"net/url"
+	"os"
+	"path/filepath"
 	"time"
 
 	"cloud.google.com/go/compute/metadata"
@@ -17,6 +19,8 @@ import (
 	"github.com/coder/coder/cli/cliflag"
 	"github.com/coder/coder/codersdk"
 	"github.com/coder/retry"
+
+	"gopkg.in/natefinch/lumberjack.v2"
 )
 
 func workspaceAgent() *cobra.Command {
@@ -36,7 +40,13 @@ func workspaceAgent() *cobra.Command {
 			if err != nil {
 				return xerrors.Errorf("parse %q: %w", rawURL, err)
 			}
-			logger := slog.Make(sloghuman.Sink(cmd.OutOrStdout())).Leveled(slog.LevelDebug)
+
+			logWriter := &lumberjack.Logger{
+				Filename: filepath.Join(os.TempDir(), "coder-agent.log"),
+				MaxSize:  5, // MB
+			}
+			defer logWriter.Close()
+			logger := slog.Make(sloghuman.Sink(cmd.ErrOrStderr()), sloghuman.Sink(logWriter)).Leveled(slog.LevelDebug)
 			client := codersdk.New(coderURL)
 
 			// exchangeToken returns a session token.
diff --git a/go.mod b/go.mod
index e5eb0c7e84770..af84af81c96df 100644
--- a/go.mod
+++ b/go.mod
@@ -67,7 +67,6 @@ require (
 	github.com/golang-migrate/migrate/v4 v4.15.2
 	github.com/google/go-github/v43 v43.0.1-0.20220414155304-00e42332e405
 	github.com/google/uuid v1.3.0
-	github.com/hashicorp/go-syslog v1.0.0
 	github.com/hashicorp/go-version v1.4.0
 	github.com/hashicorp/hc-install v0.3.1
 	github.com/hashicorp/hcl/v2 v2.12.0
@@ -115,6 +114,7 @@ require (
 	google.golang.org/api v0.75.0
 	google.golang.org/protobuf v1.28.0
 	gopkg.in/DataDog/dd-trace-go.v1 v1.38.0
+	gopkg.in/natefinch/lumberjack.v2 v2.0.0
 	k8s.io/utils v0.0.0-20220210201930-3a6ce19ff2f9
 	nhooyr.io/websocket v1.8.7
 	storj.io/drpc v0.0.30
diff --git a/go.sum b/go.sum
index 92f4ac0ffb1c6..0aac27f4608f9 100644
--- a/go.sum
+++ b/go.sum
@@ -97,6 +97,7 @@ github.com/Azure/go-autorest/tracing v0.5.0/go.mod h1:r/s2XiOKccPW3HrqB+W0TQzfbt
 github.com/Azure/go-autorest/tracing v0.6.0/go.mod h1:+vhtPC754Xsa23ID7GlGsrdKBpUA79WCAKPPZVC2DeU=
 github.com/Azure/go-ntlmssp v0.0.0-20200615164410-66371956d46c h1:/IBSNwUN8+eKzUzbJPqhK839ygXJ82sde8x3ogr6R28=
 github.com/Azure/go-ntlmssp v0.0.0-20200615164410-66371956d46c/go.mod h1:chxPXzSsl7ZWRAuOIE23GDNzjWuZquvFlgA8xmpunjU=
+github.com/BurntSushi/toml v0.3.1 h1:WXkYYl6Yr3qBf1K79EBnL4mak0OimBfB0XUf9Vl28OQ=
 github.com/BurntSushi/toml v0.3.1/go.mod h1:xHWCNGjB5oqiDr8zfno3MHue2Ht5sIBksp03qcyfWMU=
 github.com/BurntSushi/xgb v0.0.0-20160522181843-27f122750802/go.mod h1:IVnqGOEym/WlBOVXweHU+Q+/VP0lqqI8lqeDx9IjBqo=
 github.com/ClickHouse/clickhouse-go v1.4.3/go.mod h1:EaI/sW7Azgz9UATzd5ZdZHRUhHgv5+JMS9NSr2smCJI=
@@ -927,7 +928,6 @@ github.com/hashicorp/go-rootcerts v1.0.0/go.mod h1:K6zTfqpRlCUIjkwsN4Z+hiSfzSTQa
 github.com/hashicorp/go-rootcerts v1.0.2/go.mod h1:pqUvnprVnM5bf7AOirdbb01K4ccR319Vf4pU3K5EGc8=
 github.com/hashicorp/go-sockaddr v1.0.0/go.mod h1:7Xibr9yA9JjQq1JpNB2Vw7kxv8xerXegt+ozgdvDeDU=
 github.com/hashicorp/go-sockaddr v1.0.2/go.mod h1:rB4wwRAUzs07qva3c5SdrY/NEtAUjGlgmH/UkBUC97A=
-github.com/hashicorp/go-syslog v1.0.0 h1:KaodqZuhUoZereWVIYmpUgZysurB1kBLX2j0MwMrUAE=
 github.com/hashicorp/go-syslog v1.0.0/go.mod h1:qPfqrKkXGihmCqbJM2mZgkZGvKG1dFdvsLplgctolz4=
 github.com/hashicorp/go-uuid v1.0.0/go.mod h1:6SBZvOh/SIDV7/2o3Jml5SYk/TvGqwFJ/bN7x4byOro=
 github.com/hashicorp/go-uuid v1.0.1/go.mod h1:6SBZvOh/SIDV7/2o3Jml5SYk/TvGqwFJ/bN7x4byOro=
@@ -2516,6 +2516,7 @@ gopkg.in/ini.v1 v1.51.0/go.mod h1:pNLf8WUiyNEtQjuu5G5vTm06TEv9tsIgeAvK8hOrP4k=
 gopkg.in/ini.v1 v1.62.0 h1:duBzk771uxoUuOlyRLkHsygud9+5lrlGjdFBb4mSKDU=
 gopkg.in/ini.v1 v1.62.0/go.mod h1:pNLf8WUiyNEtQjuu5G5vTm06TEv9tsIgeAvK8hOrP4k=
 gopkg.in/jinzhu/gorm.v1 v1.9.1/go.mod h1:56JJPUzbikvTVnoyP1nppSkbJ2L8sunqTBDY2fDrmFg=
+gopkg.in/natefinch/lumberjack.v2 v2.0.0 h1:1Lc07Kr7qY4U2YPouBjpCLxpiyxIVoxqXgkXLknAOE8=
 gopkg.in/natefinch/lumberjack.v2 v2.0.0/go.mod h1:l0ndWWf7gzL7RNwBG7wST/UCcT4T24xpD6X8LsfU/+k=
 gopkg.in/olivere/elastic.v3 v3.0.75/go.mod h1:yDEuSnrM51Pc8dM5ov7U8aI/ToR3PG0llA8aRv2qmw0=
 gopkg.in/olivere/elastic.v5 v5.0.84/go.mod h1:LXF6q9XNBxpMqrcgax95C6xyARXWbbCXUrtTxrNrxJI=