diff --git a/tsdb/engine/tsm1/compact.go b/tsdb/engine/tsm1/compact.go
index 83351636223..51b98f6c252 100644
--- a/tsdb/engine/tsm1/compact.go
+++ b/tsdb/engine/tsm1/compact.go
@@ -508,7 +508,7 @@ func (c *Compactor) writeNewFiles(generation, sequence int, iter KeyIterator) ([
 
 		// We've hit the max file limit and there is more to write.  Create a new file
 		// and continue.
-		if err == errMaxFileExceeded {
+		if err == errMaxFileExceeded || err == ErrMaxBlocksExceeded {
 			files = append(files, fileName)
 			continue
 		} else if err == ErrNoValues {
@@ -573,7 +573,16 @@ func (c *Compactor) write(path string, iter KeyIterator) (err error) {
 		}
 
 		// Write the key and value
-		if err := w.WriteBlock(key, minTime, maxTime, block); err != nil {
+		err = w.WriteBlock(key, minTime, maxTime, block)
+		if err == ErrMaxBlocksExceeded {
+			if err := w.WriteIndex(); err != nil {
+				return err
+			}
+
+			return ErrMaxBlocksExceeded
+		}
+
+		if err != nil {
 			return err
 		}
 
diff --git a/tsdb/engine/tsm1/compact_test.go b/tsdb/engine/tsm1/compact_test.go
index 5084ac847b8..d6a60501e4c 100644
--- a/tsdb/engine/tsm1/compact_test.go
+++ b/tsdb/engine/tsm1/compact_test.go
@@ -562,6 +562,85 @@ func TestCompactor_CompactFull_TombstonedMultipleRanges(t *testing.T) {
 	}
 }
 
+// Ensures that a compaction will properly rollover to a new file when the
+// max keys per blocks is exceeded
+func TestCompactor_CompactFull_MaxKeys(t *testing.T) {
+	if testing.Short() {
+		t.Skip("Skipping max keys compaction test")
+	}
+	dir := MustTempDir()
+	defer os.RemoveAll(dir)
+
+	// write two files where the first contains a single key with the maximum
+	// number of full blocks that can fit in a TSM file
+	f1, f1Name := MustTSMWriter(dir, 1)
+	values := make([]tsm1.Value, 1000)
+	for i := 0; i < 65535; i++ {
+		values = values[:0]
+		for j := 0; j < 1000; j++ {
+			values = append(values, tsm1.NewValue(int64(i*1000+j), float64(j)))
+		}
+		if err := f1.Write("cpu,host=A#!~#value", values); err != nil {
+			t.Fatalf("write tsm f1: %v", err)
+		}
+	}
+	if err := f1.WriteIndex(); err != nil {
+		t.Fatalf("write index f1: %v", err)
+	}
+	f1.Close()
+
+	// Write a new file with 1 block that when compacted would exceed the max
+	// blocks
+	lastTimeStamp := values[len(values)-1].UnixNano()
+	values = values[:0]
+	f2, f2Name := MustTSMWriter(dir, 2)
+	for j := lastTimeStamp; j < lastTimeStamp+1000; j++ {
+		values = append(values, tsm1.NewValue(int64(j), float64(j)))
+	}
+	if err := f2.Write("cpu,host=A#!~#value", values); err != nil {
+		t.Fatalf("write tsm f1: %v", err)
+	}
+
+	if err := f2.WriteIndex(); err != nil {
+		t.Fatalf("write index f2: %v", err)
+	}
+	f2.Close()
+
+	compactor := &tsm1.Compactor{
+		Dir:       dir,
+		FileStore: &fakeFileStore{},
+	}
+
+	// Compact both files, should get 2 files back
+	files, err := compactor.CompactFull([]string{f1Name, f2Name})
+	if err != nil {
+		t.Fatalf("unexpected error writing snapshot: %v", err)
+	}
+
+	if got, exp := len(files), 2; got != exp {
+		t.Fatalf("files length mismatch: got %v, exp %v", got, exp)
+	}
+
+	expGen, expSeq, err := tsm1.ParseTSMFileName(f2Name)
+	if err != nil {
+		t.Fatalf("unexpected error parsing file name: %v", err)
+	}
+	expSeq = expSeq + 1
+
+	gotGen, gotSeq, err := tsm1.ParseTSMFileName(files[0])
+	if err != nil {
+		t.Fatalf("unexpected error parsing file name: %v", err)
+	}
+
+	if gotGen != expGen {
+		t.Fatalf("wrong generation for new file: got %v, exp %v", gotGen, expGen)
+	}
+
+	if gotSeq != expSeq {
+		t.Fatalf("wrong sequence for new file: got %v, exp %v", gotSeq, expSeq)
+	}
+}
+
 // Tests that a single TSM file can be read and iterated over
 func TestTSMKeyIterator_Single(t *testing.T) {
 	dir := MustTempDir()
@@ -1399,7 +1478,7 @@ func MustWALSegment(dir string, entries []tsm1.WALEntry) *tsm1.WALSegmentReader
 	return tsm1.NewWALSegmentReader(f)
 }
 
-func MustWriteTSM(dir string, gen int, values map[string][]tsm1.Value) string {
+func MustTSMWriter(dir string, gen int) (tsm1.TSMWriter, string) {
 	f := MustTempFile(dir)
 	oldName := f.Name()
 
@@ -1425,6 +1504,12 @@ func MustWriteTSM(dir string, gen int, values map[string][]tsm1.Value) string {
 		panic(fmt.Sprintf("create TSM writer: %v", err))
 	}
 
+	return w, newName
+}
+
+func MustWriteTSM(dir string, gen int, values map[string][]tsm1.Value) string {
+	w, name := MustTSMWriter(dir, gen)
+
 	for k, v := range values {
 		if err := w.Write(k, v); err != nil {
 			panic(fmt.Sprintf("write TSM value: %v", err))
@@ -1439,7 +1524,7 @@ func MustWriteTSM(dir string, gen int, values map[string][]tsm1.Value) string {
 		panic(fmt.Sprintf("write TSM close: %v", err))
 	}
 
-	return newName
+	return name
 }
 
 func MustTSMReader(dir string, gen int, values map[string][]tsm1.Value) *tsm1.TSMReader {
diff --git a/tsdb/engine/tsm1/writer.go b/tsdb/engine/tsm1/writer.go
index 5b488b07c88..4474c217764 100644
--- a/tsdb/engine/tsm1/writer.go
+++ b/tsdb/engine/tsm1/writer.go
@@ -102,6 +102,7 @@ var (
 	ErrNoValues             = fmt.Errorf("no values written")
 	ErrTSMClosed            = fmt.Errorf("tsm file closed")
 	ErrMaxKeyLengthExceeded = fmt.Errorf("max key length exceeded")
+	ErrMaxBlocksExceeded    = fmt.Errorf("max blocks exceeded")
 )
 
 // TSMWriter writes TSM formatted key and values.
@@ -471,6 +472,9 @@ func (t *tsmWriter) Write(key string, values Values) error {
 	return nil
 }
 
+// WriteBlock writes block for the given key and time range to the TSM file.  If the write
+// exceeds max entries for a given key, ErrMaxBlocksExceeded is returned.  This indicates
+// that the index is now full for this key and no future writes to this key will succeed.
 func (t *tsmWriter) WriteBlock(key string, minTime, maxTime int64, block []byte) error {
 	// Nothing to write
 	if len(block) == 0 {
@@ -509,6 +513,10 @@ func (t *tsmWriter) WriteBlock(key string, minTime, maxTime int64, block []byte)
 	// Increment file position pointer (checksum + block len)
 	t.n += int64(n)
 
+	if len(t.index.Entries(key)) >= maxIndexEntries {
+		return ErrMaxBlocksExceeded
+	}
+
 	return nil
 }