diff --git a/app/src/main/java/org/thoughtcrime/securesms/database/LogDatabase.kt b/app/src/main/java/org/thoughtcrime/securesms/database/LogDatabase.kt
index 2b192abf7..620777c1f 100644
--- a/app/src/main/java/org/thoughtcrime/securesms/database/LogDatabase.kt
+++ b/app/src/main/java/org/thoughtcrime/securesms/database/LogDatabase.kt
@@ -8,6 +8,7 @@ import net.zetetic.database.sqlcipher.SQLiteDatabase
 import net.zetetic.database.sqlcipher.SQLiteOpenHelper
 import org.signal.core.util.CursorUtil
 import org.signal.core.util.SqlUtil
+import org.signal.core.util.getTableRowCount
 import org.signal.core.util.logging.Log
 import org.thoughtcrime.securesms.crypto.DatabaseSecret
 import org.thoughtcrime.securesms.crypto.DatabaseSecretProvider
@@ -16,6 +17,7 @@ import org.thoughtcrime.securesms.util.ByteUnit
 import org.thoughtcrime.securesms.util.Stopwatch
 import java.io.Closeable
 import java.util.concurrent.TimeUnit
+import kotlin.math.abs
 
 /**
  * Stores logs.
@@ -164,7 +166,13 @@ class LogDatabase private constructor(
     stopwatch.split("keepers-size")
 
     if (remainingSize <= 0) {
-      writableDatabase.delete(TABLE_NAME, "$KEEP_LONGER = ?", arrayOf("0"))
+      if (abs(remainingSize) > MAX_FILE_SIZE / 2) {
+        // Not only are KEEP_LONGER logs putting us over the storage limit, it's doing it by a lot! Delete half.
+        val logCount = readableDatabase.getTableRowCount(TABLE_NAME)
+        writableDatabase.execSQL("DELETE FROM $TABLE_NAME WHERE $ID < (SELECT MAX($ID) FROM (SELECT $ID FROM $TABLE_NAME LIMIT ${logCount / 2}))")
+      } else {
+        writableDatabase.delete(TABLE_NAME, "$KEEP_LONGER = ?", arrayOf("0"))
+      }
       return
     }
 
diff --git a/core-util/src/main/java/org/signal/core/util/SQLiteDatabaseExtensions.kt b/core-util/src/main/java/org/signal/core/util/SQLiteDatabaseExtensions.kt
new file mode 100644
index 000000000..c7176cf58
--- /dev/null
+++ b/core-util/src/main/java/org/signal/core/util/SQLiteDatabaseExtensions.kt
@@ -0,0 +1,13 @@
+package org.signal.core.util
+
+import androidx.sqlite.db.SupportSQLiteDatabase
+
+fun SupportSQLiteDatabase.getTableRowCount(table: String): Int {
+  return this.query("SELECT COUNT(*) FROM $table").use {
+    if (it.moveToFirst()) {
+      it.getInt(0)
+    } else {
+      0
+    }
+  }
+}
\ No newline at end of file