diff --git a/src/Agent/AutopilotMonitor.Agent.V2.Core.Tests/Logging/AgentLoggerTests.cs b/src/Agent/AutopilotMonitor.Agent.V2.Core.Tests/Logging/AgentLoggerTests.cs
new file mode 100644
index 00000000..b20b59f4
--- /dev/null
+++ b/src/Agent/AutopilotMonitor.Agent.V2.Core.Tests/Logging/AgentLoggerTests.cs
@@ -0,0 +1,114 @@
+#nullable enable
+using System;
+using System.IO;
+using System.Linq;
+using AutopilotMonitor.Agent.V2.Core.Logging;
+using AutopilotMonitor.Agent.V2.Core.Tests.Harness;
+using Xunit;
+
+namespace AutopilotMonitor.Agent.V2.Core.Tests.Logging
+{
+    /// <summary>
+    /// PR2: file-size cap rotation. Long-running verbose sessions used to grow the daily log
+    /// into hundreds of MB; the logger now rolls over to a numeric suffix once a segment
+    /// reaches the cap, keeping every byte but in manageable files.
+    /// </summary>
+    public sealed class AgentLoggerTests
+    {
+        private static string TodayBaseName => $"agent_{DateTime.Now:yyyyMMdd}";
+
+        [Fact]
+        public void Log_writes_to_unsuffixed_base_file_when_dir_is_empty()
+        {
+            using var tmp = new TempDirectory();
+            var logger = new AgentLogger(tmp.Path, AgentLogLevel.Info, maxFileSizeBytes: 1024L * 1024);
+
+            logger.Info("hello");
+
+            var basePath = Path.Combine(tmp.Path, TodayBaseName + ".log");
+            Assert.True(File.Exists(basePath), $"expected base file at {basePath}");
+            Assert.Contains("hello", File.ReadAllText(basePath));
+        }
+
+        [Fact]
+        public void Log_rotates_when_active_segment_crosses_cap()
+        {
+            using var tmp = new TempDirectory();
+            // 1 KB cap so rotation triggers after a few writes.
+            var logger = new AgentLogger(tmp.Path, AgentLogLevel.Info, maxFileSizeBytes: 1024);
+
+            // Each line ~80 bytes after timestamp/severity envelope; 30 lines clears 1 KB
+            // even at the smallest payload. The first lines fill the base file; once the
+            // FileInfo.Length read sees >= 1024 the next call rotates to _002.
+            for (int i = 0; i < 60; i++)
+            {
+                logger.Info($"line-{i:D4}-padded-with-some-extra-context-to-cross-1KB-quickly");
+            }
+
+            var files = Directory.GetFiles(tmp.Path, TodayBaseName + "*.log").OrderBy(s => s).ToArray();
+            Assert.True(files.Length >= 2, $"expected at least 2 segments, got: {string.Join(",", files.Select(Path.GetFileName))}");
+
+            // The unsuffixed file is the first segment; rotated segments use _002 onward.
+            var rotated = files.FirstOrDefault(p => Path.GetFileNameWithoutExtension(p).EndsWith("_002"));
+            Assert.NotNull(rotated);
+        }
+
+        [Fact]
+        public void Log_writes_rotation_marker_as_first_line_of_new_segment()
+        {
+            using var tmp = new TempDirectory();
+            var logger = new AgentLogger(tmp.Path, AgentLogLevel.Info, maxFileSizeBytes: 1024);
+
+            for (int i = 0; i < 60; i++)
+            {
+                logger.Info($"pad-{i:D4}-content-content-content-content-content-content");
+            }
+
+            var rotatedPath = Path.Combine(tmp.Path, TodayBaseName + "_002.log");
+            Assert.True(File.Exists(rotatedPath), "expected agent_YYYYMMDD_002.log to exist");
+            var first = File.ReadAllLines(rotatedPath).FirstOrDefault();
+            Assert.NotNull(first);
+            Assert.Contains("AgentLogger: rotated", first);
+        }
+
+        [Fact]
+        public void Log_continues_existing_rotation_on_restart_without_overwriting()
+        {
+            using var tmp = new TempDirectory();
+            // Pre-seed: looks like an earlier process already rotated up to _003.
+            File.WriteAllText(Path.Combine(tmp.Path, TodayBaseName + ".log"), "older-base\n");
+            File.WriteAllText(Path.Combine(tmp.Path, TodayBaseName + "_002.log"), "older-002\n");
+            File.WriteAllText(Path.Combine(tmp.Path, TodayBaseName + "_003.log"), "older-003\n");
+
+            var logger = new AgentLogger(tmp.Path, AgentLogLevel.Info, maxFileSizeBytes: 1024L * 1024);
+            logger.Info("after-restart");
+
+            // New entries must land in the highest existing segment (_003), not in a fresh
+            // base file. Older content in _003 must be preserved.
+            var resumed = File.ReadAllText(Path.Combine(tmp.Path, TodayBaseName + "_003.log"));
+            Assert.Contains("older-003", resumed);
+            Assert.Contains("after-restart", resumed);
+
+            // Older segments are left alone.
+            Assert.Equal("older-base\n", File.ReadAllText(Path.Combine(tmp.Path, TodayBaseName + ".log")));
+            Assert.Equal("older-002\n", File.ReadAllText(Path.Combine(tmp.Path, TodayBaseName + "_002.log")));
+        }
+
+        [Fact]
+        public void Log_swallows_io_errors_silently()
+        {
+            using var tmp = new TempDirectory();
+            var logger = new AgentLogger(tmp.Path, AgentLogLevel.Info, maxFileSizeBytes: 1024L * 1024);
+
+            // Hold an exclusive lock on today's file to force AppendAllText to throw.
+            var lockedPath = Path.Combine(tmp.Path, TodayBaseName + ".log");
+            File.WriteAllText(lockedPath, ""); // ensure exists
+            using var holder = new FileStream(lockedPath, FileMode.Open, FileAccess.ReadWrite, FileShare.None);
+
+            // Must NOT throw — logger swallows IO errors to keep the agent running.
+            logger.Info("dropped");
+            // No assertion needed beyond "did not throw"; the regression we guard against is
+            // the original swallow-all behaviour, which the rotation refactor must preserve.
+        }
+    }
+}
diff --git a/src/Agent/AutopilotMonitor.Agent.V2.Core/Logging/AgentLogger.cs b/src/Agent/AutopilotMonitor.Agent.V2.Core/Logging/AgentLogger.cs
index f1f11070..3883a3d3 100644
--- a/src/Agent/AutopilotMonitor.Agent.V2.Core/Logging/AgentLogger.cs
+++ b/src/Agent/AutopilotMonitor.Agent.V2.Core/Logging/AgentLogger.cs
@@ -23,27 +23,82 @@ namespace AutopilotMonitor.Agent.V2.Core.Logging
     /// </summary>
     public class AgentLogger
     {
-        private readonly string _logFilePath;
+        // Rotation cap. With per-enrollment lifecycle (30 min – 4 h) and verbose mode the
+        // active log can grow into the hundreds of MB territory; 50 MB keeps individual
+        // files manageable for forensics tooling without hiding any data — rotated files
+        // are kept alongside the active one with a numeric suffix.
+        private const long DefaultMaxFileSizeBytes = 50L * 1024 * 1024;
+
         private AgentLogLevel _logLevel;
         private readonly object _lockObject = new object();
 
+        private readonly long _maxFileSizeBytes;
+        private readonly string _logDirectory;
+        private readonly string _logFileBaseName;   // "agent_20260425"
+        private string _logFilePath;                // mutable — rotates to "_002", "_003" ...
+        private int _rotationSuffix;                // 0 = base file, 2+ = "_002" etc.
+
         /// <summary>
         /// When true, log entries are also written to Console.Out (same format as the log file).
         /// Set via --console flag or programmatically.
         /// </summary>
         public bool EnableConsoleOutput { get; set; }
 
-        public AgentLogger(string logDirectory, AgentLogLevel logLevel = AgentLogLevel.Info)
+        public AgentLogger(string logDirectory, AgentLogLevel logLevel = AgentLogLevel.Info, long maxFileSizeBytes = DefaultMaxFileSizeBytes)
         {
             _logLevel = logLevel;
+            _maxFileSizeBytes = maxFileSizeBytes > 0 ? maxFileSizeBytes : DefaultMaxFileSizeBytes;
+            _logDirectory = logDirectory;
 
             if (!Directory.Exists(logDirectory))
             {
                 Directory.CreateDirectory(logDirectory);
             }
 
-            var logFileName = $"agent_{DateTime.Now:yyyyMMdd}.log";
-            _logFilePath = Path.Combine(logDirectory, logFileName);
+            _logFileBaseName = $"agent_{DateTime.Now:yyyyMMdd}";
+            _rotationSuffix = ProbeNextRotationSuffix(logDirectory, _logFileBaseName);
+            _logFilePath = BuildLogFilePath();
+        }
+
+        // Picks up the highest existing rotation suffix on the same day so a process restart
+        // doesn't overwrite previous segments. Returns 0 when no log file exists yet — the
+        // first segment uses the unsuffixed name `agent_YYYYMMDD.log`.
+        private static int ProbeNextRotationSuffix(string dir, string baseName)
+        {
+            if (!Directory.Exists(dir)) return 0;
+            string[] existing;
+            try { existing = Directory.GetFiles(dir, baseName + "*.log"); }
+            catch { return 0; }
+
+            int max = 0;
+            foreach (var path in existing)
+            {
+                var name = Path.GetFileNameWithoutExtension(path);
+                if (string.Equals(name, baseName, StringComparison.OrdinalIgnoreCase))
+                {
+                    if (max < 1) max = 1;
+                    continue;
+                }
+                if (name.Length > baseName.Length + 1 &&
+                    name.StartsWith(baseName + "_", StringComparison.OrdinalIgnoreCase) &&
+                    int.TryParse(name.Substring(baseName.Length + 1), out var suffix) &&
+                    suffix > max)
+                {
+                    max = suffix;
+                }
+            }
+            // 0 means "no file yet" → use the unsuffixed base; otherwise continue at the
+            // highest existing suffix so the active writer appends to the most recent file
+            // (rotation kicks in once it crosses the cap).
+            return max;
+        }
+
+        private string BuildLogFilePath()
+        {
+            var name = _rotationSuffix < 2
+                ? $"{_logFileBaseName}.log"
+                : $"{_logFileBaseName}_{_rotationSuffix:D3}.log";
+            return Path.Combine(_logDirectory, name);
         }
 
         /// <summary>
@@ -99,6 +154,8 @@ namespace AutopilotMonitor.Agent.V2.Core.Logging
                     var timestamp = DateTime.UtcNow.ToString("yyyy-MM-dd HH:mm:ss.fff");
                     var logEntry = $"[{timestamp}] [{level}] {SanitizeLogMessage(message)}";
 
+                    RotateIfOverCap(timestamp);
+
                     File.AppendAllText(_logFilePath, logEntry + Environment.NewLine);
 
                     if (EnableConsoleOutput)
@@ -113,6 +170,30 @@ namespace AutopilotMonitor.Agent.V2.Core.Logging
             }
         }
 
+        // Best-effort size check. FileInfo.Length is briefly cached, so under bursty writes
+        // the active file can drift slightly past the cap before rotation kicks in — that's
+        // acceptable. Rotation is non-fatal: any failure here is silently ignored so the
+        // logger never breaks the agent.
+        private void RotateIfOverCap(string timestamp)
+        {
+            try
+            {
+                var fi = new FileInfo(_logFilePath);
+                if (!fi.Exists || fi.Length < _maxFileSizeBytes) return;
+
+                _rotationSuffix = _rotationSuffix < 2 ? 2 : _rotationSuffix + 1;
+                _logFilePath = BuildLogFilePath();
+
+                var capMb = _maxFileSizeBytes / (1024 * 1024);
+                var rotateMsg = $"[{timestamp}] [INFO] AgentLogger: rotated from previous segment ({capMb}MB cap reached).";
+                File.AppendAllText(_logFilePath, rotateMsg + Environment.NewLine);
+            }
+            catch
+            {
+                // Best-effort: never break logging on a rotation glitch.
+            }
+        }
+
         /// <summary>
         /// Sanitizes log messages to prevent log injection attacks.
         /// Escapes control characters that could forge log entries.
diff --git a/src/Agent/AutopilotMonitor.Agent.V2/buildcounter.txt b/src/Agent/AutopilotMonitor.Agent.V2/buildcounter.txt
index ec6cab01..55bd0ac4 100644
--- a/src/Agent/AutopilotMonitor.Agent.V2/buildcounter.txt
+++ b/src/Agent/AutopilotMonitor.Agent.V2/buildcounter.txt
@@ -1 +1 @@
-331
+333
diff --git a/src/Agent/AutopilotMonitor.Agent/buildcounter.txt b/src/Agent/AutopilotMonitor.Agent/buildcounter.txt
index afe5b3bb..378d4b14 100644
--- a/src/Agent/AutopilotMonitor.Agent/buildcounter.txt
+++ b/src/Agent/AutopilotMonitor.Agent/buildcounter.txt
@@ -1 +1 @@
-1161
+1162