diff --git a/CHANGES.txt b/CHANGES.txt
index 430654948a..4a7d8ca817 100644
--- a/CHANGES.txt
+++ b/CHANGES.txt
@@ -99,6 +99,7 @@
  * Log failed host when preparing incremental repair (CASSANDRA-8228)
  * Force config client mode in CQLSSTableWriter (CASSANDRA-8281)
 Merged from 2.0:
+ * Check for available disk space before starting a compaction (CASSANDRA-8562)
  * Fix DISTINCT queries with LIMITs or paging when some partitions
    contain only tombstones (CASSANDRA-8490)
  * Introduce background cache refreshing to permissions cache
diff --git a/src/java/org/apache/cassandra/db/Directories.java b/src/java/org/apache/cassandra/db/Directories.java
index 4c4078c106..fa9b3206e7 100644
--- a/src/java/org/apache/cassandra/db/Directories.java
+++ b/src/java/org/apache/cassandra/db/Directories.java
@@ -345,6 +345,24 @@ public class Directories
         Collections.sort(candidates);
     }
 
+    public boolean hasAvailableDiskSpace(long estimatedSSTables, long expectedTotalWriteSize)
+    {
+        long writeSize = expectedTotalWriteSize / estimatedSSTables;
+        long totalAvailable = 0L;
+
+        for (DataDirectory dataDir : dataDirectories)
+        {
+            if (BlacklistedDirectories.isUnwritable(getLocationForDisk(dataDir)))
+                  continue;
+            DataDirectoryCandidate candidate = new DataDirectoryCandidate(dataDir);
+            // exclude directory if its total writeSize does not fit to data directory
+            if (candidate.availableSpace < writeSize)
+                continue;
+            totalAvailable += candidate.availableSpace;
+        }
+        return totalAvailable > expectedTotalWriteSize;
+    }
+
     public static File getSnapshotDirectory(Descriptor desc, String snapshotName)
     {
         return getSnapshotDirectory(desc.directory, snapshotName);
diff --git a/src/java/org/apache/cassandra/db/compaction/CompactionTask.java b/src/java/org/apache/cassandra/db/compaction/CompactionTask.java
index 8b5058be18..dfbdc22946 100644
--- a/src/java/org/apache/cassandra/db/compaction/CompactionTask.java
+++ b/src/java/org/apache/cassandra/db/compaction/CompactionTask.java
@@ -19,6 +19,7 @@ package org.apache.cassandra.db.compaction;
 
 import java.io.File;
 import java.io.IOException;
+import java.util.Arrays;
 import java.util.Collection;
 import java.util.HashMap;
 import java.util.Iterator;
@@ -88,12 +89,14 @@ public class CompactionTask extends AbstractCompactionTask
             logger.warn("insufficient space to compact all requested files {}", StringUtils.join(sstables, ", "));
             // Note that we have removed files that are still marked as compacting.
             // This suboptimal but ok since the caller will unmark all the sstables at the end.
-            return sstables.remove(cfs.getMaxSizeFile(sstables));
-        }
-        else
-        {
-            return false;
+            SSTableReader removedSSTable = cfs.getMaxSizeFile(sstables);
+            if (sstables.remove(removedSSTable))
+            {
+                cfs.getDataTracker().unmarkCompacting(Arrays.asList(removedSSTable));
+                return true;
+            }
         }
+        return false;
     }
 
     /**
@@ -117,6 +120,11 @@ public class CompactionTask extends AbstractCompactionTask
         if (DatabaseDescriptor.isSnapshotBeforeCompaction())
             cfs.snapshotWithoutFlush(System.currentTimeMillis() + "-compact-" + cfs.name);
 
+        // note that we need to do a rough estimate early if we can fit the compaction on disk - this is pessimistic, but
+        // since we might remove sstables from the compaction in checkAvailableDiskSpace it needs to be done here
+        long earlySSTableEstimate = Math.max(1, cfs.getExpectedCompactedFileSize(sstables, compactionType) / strategy.getMaxSSTableBytes());
+        checkAvailableDiskSpace(earlySSTableEstimate);
+
         // sanity check: all sstables must belong to the same cfs
         assert !Iterables.any(sstables, new Predicate<SSTableReader>()
         {
@@ -149,7 +157,7 @@ public class CompactionTask extends AbstractCompactionTask
             Set<SSTableReader> actuallyCompact = Sets.difference(sstables, controller.getFullyExpiredSSTables());
 
             long estimatedTotalKeys = Math.max(cfs.metadata.getMinIndexInterval(), SSTableReader.getApproximateKeyCount(actuallyCompact));
-            long estimatedSSTables = Math.max(1, SSTableReader.getTotalBytes(actuallyCompact) / strategy.getMaxSSTableBytes());
+            long estimatedSSTables = Math.max(1, cfs.getExpectedCompactedFileSize(actuallyCompact, compactionType) / strategy.getMaxSSTableBytes());
             long keysPerSSTable = (long) Math.ceil((double) estimatedTotalKeys / estimatedSSTables);
             SSTableFormat.Type sstableFormat = getFormatType(sstables);
 
@@ -278,6 +286,15 @@ public class CompactionTask extends AbstractCompactionTask
         return minRepairedAt;
     }
 
+    protected void checkAvailableDiskSpace(long estimatedSSTables)
+    {
+        while (!getDirectories().hasAvailableDiskSpace(estimatedSSTables, getExpectedWriteSize()))
+        {
+            if (!reduceScopeForLimitedSpace())
+                throw new RuntimeException(String.format("Not enough space for compaction, estimated sstables = %d, expected write size = %d", estimatedSSTables, getExpectedWriteSize()));
+        }
+    }
+
     private SSTableWriter createCompactionWriter(File sstableDirectory, long keysPerSSTable, long repairedAt, SSTableFormat.Type type)
     {
         return SSTableWriter.create(Descriptor.fromFilename(cfs.getTempSSTablePath(sstableDirectory), type),
diff --git a/src/java/org/apache/cassandra/io/util/DiskAwareRunnable.java b/src/java/org/apache/cassandra/io/util/DiskAwareRunnable.java
index 4188f6e3fc..925efd68ac 100644
--- a/src/java/org/apache/cassandra/io/util/DiskAwareRunnable.java
+++ b/src/java/org/apache/cassandra/io/util/DiskAwareRunnable.java
@@ -24,13 +24,7 @@ public abstract class DiskAwareRunnable extends WrappedRunnable
 {
     protected Directories.DataDirectory getWriteDirectory(long writeSize)
     {
-        Directories.DataDirectory directory;
-        while (true)
-        {
-            directory = getDirectories().getWriteableLocation(writeSize);
-            if (directory != null || !reduceScopeForLimitedSpace())
-                break;
-        }
+        Directories.DataDirectory directory = getDirectories().getWriteableLocation(writeSize);
         if (directory == null)
             throw new RuntimeException("Insufficient disk space to write " + writeSize + " bytes");
 
@@ -42,13 +36,4 @@ public abstract class DiskAwareRunnable extends WrappedRunnable
      * @return Directories instance for the CF.
      */
     protected abstract Directories getDirectories();
-
-    /**
-     * Called if no disk is available with free space for the full write size.
-     * @return true if the scope of the task was successfully reduced.
-     */
-    public boolean reduceScopeForLimitedSpace()
-    {
-        return false;
-    }
 }