diff --git a/app/lifecycle/logging.go b/app/lifecycle/logging.go
index df2597a8..a8f1f7cd 100644
--- a/app/lifecycle/logging.go
+++ b/app/lifecycle/logging.go
@@ -5,6 +5,8 @@ import (
 	"log/slog"
 	"os"
 	"path/filepath"
+	"strconv"
+	"strings"
 
 	"github.com/ollama/ollama/envconfig"
 )
@@ -24,6 +26,7 @@ func InitLogging() {
 		logFile = os.Stderr
 		// TODO - write one-line to the app.log file saying we're running in console mode to help avoid confusion
 	} else {
+		rotateLogs(AppLogFile)
 		logFile, err = os.OpenFile(AppLogFile, os.O_APPEND|os.O_WRONLY|os.O_CREATE, 0755)
 		if err != nil {
 			slog.Error(fmt.Sprintf("failed to create server log %v", err))
@@ -46,3 +49,32 @@ func InitLogging() {
 
 	slog.Info("ollama app started")
 }
+
+func rotateLogs(logFile string) {
+	if _, err := os.Stat(logFile); os.IsNotExist(err) {
+		return
+	}
+	index := strings.LastIndex(logFile, ".")
+	pre := logFile[:index]
+	post := "." + logFile[index+1:]
+	for i := LogRotationCount; i > 0; i-- {
+		older := pre + "-" + strconv.Itoa(i) + post
+		newer := pre + "-" + strconv.Itoa(i-1) + post
+		if i == 1 {
+			newer = pre + post
+		}
+		if _, err := os.Stat(newer); err == nil {
+			if _, err := os.Stat(older); err == nil {
+				err := os.Remove(older)
+				if err != nil {
+					slog.Warn("Failed to remove older log", "older", older, "error", err)
+					continue
+				}
+			}
+			err := os.Rename(newer, older)
+			if err != nil {
+				slog.Warn("Failed to rotate log", "older", older, "newer", newer, "error", err)
+			}
+		}
+	}
+}
diff --git a/app/lifecycle/logging_test.go b/app/lifecycle/logging_test.go
new file mode 100644
index 00000000..a2157ca2
--- /dev/null
+++ b/app/lifecycle/logging_test.go
@@ -0,0 +1,44 @@
+package lifecycle
+
+import (
+	"os"
+	"path/filepath"
+	"strconv"
+	"testing"
+
+	"github.com/stretchr/testify/assert"
+	"github.com/stretchr/testify/require"
+)
+
+func TestRotateLogs(t *testing.T) {
+	logDir := t.TempDir()
+	logFile := filepath.Join(logDir, "testlog.log")
+
+	// No log exists
+	rotateLogs(logFile)
+
+	require.NoError(t, os.WriteFile(logFile, []byte("1"), 0644))
+	assert.FileExists(t, logFile)
+	// First rotation
+	rotateLogs(logFile)
+	assert.FileExists(t, filepath.Join(logDir, "testlog-1.log"))
+	assert.NoFileExists(t, filepath.Join(logDir, "testlog-2.log"))
+	assert.NoFileExists(t, logFile)
+
+	// Should be a no-op without a new log
+	rotateLogs(logFile)
+	assert.FileExists(t, filepath.Join(logDir, "testlog-1.log"))
+	assert.NoFileExists(t, filepath.Join(logDir, "testlog-2.log"))
+	assert.NoFileExists(t, logFile)
+
+	for i := 2; i <= LogRotationCount+1; i++ {
+		require.NoError(t, os.WriteFile(logFile, []byte(strconv.Itoa(i)), 0644))
+		assert.FileExists(t, logFile)
+		rotateLogs(logFile)
+		assert.NoFileExists(t, logFile)
+		for j := 1; j < i; j++ {
+			assert.FileExists(t, filepath.Join(logDir, "testlog-"+strconv.Itoa(j)+".log"))
+		}
+		assert.NoFileExists(t, filepath.Join(logDir, "testlog-"+strconv.Itoa(i+1)+".log"))
+	}
+}
diff --git a/app/lifecycle/paths.go b/app/lifecycle/paths.go
index fe07bce1..4d9f4c5a 100644
--- a/app/lifecycle/paths.go
+++ b/app/lifecycle/paths.go
@@ -16,11 +16,12 @@ var (
 	AppDir     = "/opt/Ollama"
 	AppDataDir = "/opt/Ollama"
 	// TODO - should there be a distinct log dir?
-	UpdateStageDir = "/tmp"
-	AppLogFile     = "/tmp/ollama_app.log"
-	ServerLogFile  = "/tmp/ollama.log"
-	UpgradeLogFile = "/tmp/ollama_update.log"
-	Installer      = "OllamaSetup.exe"
+	UpdateStageDir   = "/tmp"
+	AppLogFile       = "/tmp/ollama_app.log"
+	ServerLogFile    = "/tmp/ollama.log"
+	UpgradeLogFile   = "/tmp/ollama_update.log"
+	Installer        = "OllamaSetup.exe"
+	LogRotationCount = 5
 )
 
 func init() {
diff --git a/app/lifecycle/server.go b/app/lifecycle/server.go
index 0152ccd1..c178a1ab 100644
--- a/app/lifecycle/server.go
+++ b/app/lifecycle/server.go
@@ -54,7 +54,7 @@ func start(ctx context.Context, command string) (*exec.Cmd, error) {
 		return nil, fmt.Errorf("failed to spawn server stderr pipe: %w", err)
 	}
 
-	// TODO - rotation
+	rotateLogs(ServerLogFile)
 	logFile, err := os.OpenFile(ServerLogFile, os.O_APPEND|os.O_WRONLY|os.O_CREATE, 0755)
 	if err != nil {
 		return nil, fmt.Errorf("failed to create server log: %w", err)
diff --git a/docs/troubleshooting.md b/docs/troubleshooting.md
index 60d63c7d..de29b344 100644
--- a/docs/troubleshooting.md
+++ b/docs/troubleshooting.md
@@ -22,7 +22,7 @@ docker logs <container-name>
 If manually running `ollama serve` in a terminal, the logs will be on that terminal.
 
 When you run Ollama on **Windows**, there are a few different locations. You can view them in the explorer window by hitting `<cmd>+R` and type in:
-- `explorer %LOCALAPPDATA%\Ollama` to view logs
+- `explorer %LOCALAPPDATA%\Ollama` to view logs.  The most recent server logs will be in `server.log` and older logs will be in `server-#.log` 
 - `explorer %LOCALAPPDATA%\Programs\Ollama` to browse the binaries (The installer adds this to your user PATH)
 - `explorer %HOMEPATH%\.ollama` to browse where models and configuration is stored
 - `explorer %TEMP%` where temporary executable files are stored in one or more `ollama*` directories
diff --git a/docs/windows.md b/docs/windows.md
index 832b3d43..abc0eb30 100644
--- a/docs/windows.md
+++ b/docs/windows.md
@@ -39,8 +39,8 @@ server.
 Ollama on Windows stores files in a few different locations.  You can view them in
 the explorer window by hitting `<cmd>+R` and type in:
 - `explorer %LOCALAPPDATA%\Ollama` contains logs, and downloaded updates
-    - *app.log* contains logs from the GUI application
-    - *server.log* contains the server logs
+    - *app.log* contains most resent logs from the GUI application
+    - *server.log* contains the most recent server logs
     - *upgrade.log* contains log output for upgrades
 - `explorer %LOCALAPPDATA%\Programs\Ollama` contains the binaries (The installer adds this to your user PATH)
 - `explorer %HOMEPATH%\.ollama` contains models and configuration