diff --git a/wpilibc/src/main/native/cpp/DataLogManager.cpp b/wpilibc/src/main/native/cpp/DataLogManager.cpp
index bd5e50bc54..3352d4db8e 100644
--- a/wpilibc/src/main/native/cpp/DataLogManager.cpp
+++ b/wpilibc/src/main/native/cpp/DataLogManager.cpp
@@ -4,6 +4,8 @@
 
 #include "frc/DataLogManager.h"
 
+#include <frc/Errors.h>
+
 #include <algorithm>
 #include <ctime>
 #include <random>
@@ -129,6 +131,8 @@ void Thread::Main() {
         }
         auto size = entry.file_size();
         if (fs::remove(entry.path(), ec)) {
+          FRC_ReportError(warn::Warning, "DataLogManager: Deleted {}",
+                          entry.path().string());
           freeSpace += size;
           if (freeSpace >= kFreeSpaceThreshold) {
             break;
@@ -138,6 +142,13 @@ void Thread::Main() {
                      entry.path().string());
         }
       }
+    } else if (freeSpace < 2 * kFreeSpaceThreshold) {
+      FRC_ReportError(
+          warn::Warning,
+          "DataLogManager: Log storage device has {} MB of free space "
+          "remaining! Logs will get deleted below {} MB of free space. "
+          "Consider deleting logs off the storage device.",
+          freeSpace / 1000000, kFreeSpaceThreshold / 1000000);
     }
   }
 
diff --git a/wpilibj/src/main/java/edu/wpi/first/wpilibj/DataLogManager.java b/wpilibj/src/main/java/edu/wpi/first/wpilibj/DataLogManager.java
index 76f8f7cddb..5a15468374 100644
--- a/wpilibj/src/main/java/edu/wpi/first/wpilibj/DataLogManager.java
+++ b/wpilibj/src/main/java/edu/wpi/first/wpilibj/DataLogManager.java
@@ -257,6 +257,7 @@ public final class DataLogManager {
             }
             long length = file.length();
             if (file.delete()) {
+              DriverStation.reportWarning("DataLogManager: Deleted " + file.getName(), false);
               freeSpace += length;
               if (freeSpace >= kFreeSpaceThreshold) {
                 break;
@@ -266,6 +267,15 @@ public final class DataLogManager {
             }
           }
         }
+      } else if (freeSpace < 2 * kFreeSpaceThreshold) {
+        DriverStation.reportWarning(
+            "DataLogManager: Log storage device has "
+                + freeSpace / 1000000
+                + " MB of free space remaining! Logs will get deleted below "
+                + kFreeSpaceThreshold / 1000000
+                + " MB of free space."
+                + "Consider deleting logs off the storage device.",
+            false);
       }
     }