diff --git a/src/CrossPointState.cpp b/src/CrossPointState.cpp
index 31cb2ac..91aa253 100644
--- a/src/CrossPointState.cpp
+++ b/src/CrossPointState.cpp
@@ -5,7 +5,7 @@
 #include <Serialization.h>
 
 namespace {
-constexpr uint8_t STATE_FILE_VERSION = 1;
+constexpr uint8_t STATE_FILE_VERSION = 2;
 constexpr char STATE_FILE[] = "/.crosspoint/state.bin";
 }  // namespace
 
@@ -19,6 +19,7 @@ bool CrossPointState::saveToFile() const {
 
   serialization::writePod(outputFile, STATE_FILE_VERSION);
   serialization::writeString(outputFile, openEpubPath);
+  serialization::writePod(outputFile, lastSleepImage);
   outputFile.close();
   return true;
 }
@@ -31,13 +32,18 @@ bool CrossPointState::loadFromFile() {
 
   uint8_t version;
   serialization::readPod(inputFile, version);
-  if (version != STATE_FILE_VERSION) {
+  if (version > STATE_FILE_VERSION) {
     Serial.printf("[%lu] [CPS] Deserialization failed: Unknown version %u\n", millis(), version);
     inputFile.close();
     return false;
   }
 
   serialization::readString(inputFile, openEpubPath);
+  if (version >= 2) {
+    serialization::readPod(inputFile, lastSleepImage);
+  } else {
+    lastSleepImage = 0;
+  }
 
   inputFile.close();
   return true;
diff --git a/src/CrossPointState.h b/src/CrossPointState.h
index f060a0c..87ce4e9 100644
--- a/src/CrossPointState.h
+++ b/src/CrossPointState.h
@@ -8,6 +8,7 @@ class CrossPointState {
 
  public:
   std::string openEpubPath;
+  uint8_t lastSleepImage;
   ~CrossPointState() = default;
 
   // Get singleton instance
diff --git a/src/activities/boot_sleep/SleepActivity.cpp b/src/activities/boot_sleep/SleepActivity.cpp
index 3305a16..0d3eab0 100644
--- a/src/activities/boot_sleep/SleepActivity.cpp
+++ b/src/activities/boot_sleep/SleepActivity.cpp
@@ -80,7 +80,13 @@ void SleepActivity::renderCustomSleepScreen() const {
     const auto numFiles = files.size();
     if (numFiles > 0) {
       // Generate a random number between 1 and numFiles
-      const auto randomFileIndex = random(numFiles);
+      auto randomFileIndex = random(numFiles);
+      // If we picked the same image as last time, reroll
+      while (numFiles > 1 && randomFileIndex == APP_STATE.lastSleepImage) {
+        randomFileIndex = random(numFiles);
+      }
+      APP_STATE.lastSleepImage = randomFileIndex;
+      APP_STATE.saveToFile();
       const auto filename = "/sleep/" + files[randomFileIndex];
       FsFile file;
       if (SdMan.openFileForRead("SLP", filename, file)) {
diff --git a/src/main.cpp b/src/main.cpp
index 5261df3..34e7376 100644
--- a/src/main.cpp
+++ b/src/main.cpp
@@ -303,6 +303,7 @@ void setup() {
     // Clear app state to avoid getting into a boot loop if the epub doesn't load
     const auto path = APP_STATE.openEpubPath;
     APP_STATE.openEpubPath = "";
+    APP_STATE.lastSleepImage = 0;
     APP_STATE.saveToFile();
     onGoToReader(path);
   }