diff --git a/client/driver/logging/rotator.go b/client/driver/logging/rotator.go
index bd3ed86a1fd9..152ab55086d2 100644
--- a/client/driver/logging/rotator.go
+++ b/client/driver/logging/rotator.go
@@ -2,6 +2,7 @@ package logging
 
 import (
 	"bufio"
+	"bytes"
 	"fmt"
 	"io/ioutil"
 	"log"
@@ -15,8 +16,20 @@ import (
 )
 
 const (
-	bufSize  = 32768
-	flushDur = 100 * time.Millisecond
+	// logBufferSize is the size of the buffer.
+	logBufferSize = 32 * 1024
+
+	// bufferFlushDuration is the duration at which we flush the buffer.
+	bufferFlushDuration = 100 * time.Millisecond
+
+	// lineScanLimit is the number of bytes we will attempt to scan for new
+	// lines when approaching the end of the file to avoid a log line being
+	// split between two files. Any single line that is greater than this limit
+	// may be split.
+	lineScanLimit = 16 * 1024
+
+	// newLineDelimiter is the delimiter used for new lines.
+	newLineDelimiter = '\n'
 )
 
 // FileRotator writes bytes to a rotated set of files
@@ -53,7 +66,7 @@ func NewFileRotator(path string, baseFile string, maxFiles int,
 		path:         path,
 		baseFileName: baseFile,
 
-		flushTicker: time.NewTicker(flushDur),
+		flushTicker: time.NewTicker(bufferFlushDuration),
 		logger:      logger,
 		purgeCh:     make(chan struct{}, 1),
 		doneCh:      make(chan struct{}, 1),
@@ -70,12 +83,13 @@ func NewFileRotator(path string, baseFile string, maxFiles int,
 // equal to the maximum size the user has defined.
 func (f *FileRotator) Write(p []byte) (n int, err error) {
 	n = 0
-	var nw int
+	var forceRotate bool
 
 	for n < len(p) {
 		// Check if we still have space in the current file, otherwise close and
 		// open the next file
-		if f.currentWr >= f.FileSize {
+		if forceRotate || f.currentWr >= f.FileSize {
+			forceRotate = false
 			f.flushBuffer()
 			f.currentFile.Close()
 			if err := f.nextFile(); err != nil {
@@ -83,15 +97,38 @@ func (f *FileRotator) Write(p []byte) (n int, err error) {
 				return 0, err
 			}
 		}
-		// Calculate the remaining size on this file
-		remainingSize := f.FileSize - f.currentWr
-
-		// Check if the number of bytes that we have to write is less than the
-		// remaining size of the file
-		if remainingSize < int64(len(p[n:])) {
-			// Write the number of bytes that we can write on the current file
-			li := int64(n) + remainingSize
-			nw, err = f.writeToBuffer(p[n:li])
+		// Calculate the remaining size on this file and how much we have left
+		// to write
+		remainingSpace := f.FileSize - f.currentWr
+		remainingToWrite := int64(len(p[n:]))
+
+		// Check if we are near the end of the file. If we are we attempt to
+		// avoid a log line being split between two files.
+		var nw int
+		if (remainingSpace - lineScanLimit) < remainingToWrite {
+			// Scan for new line and if the data up to new line fits in current
+			// file, write to buffer
+			idx := bytes.IndexByte(p[n:], newLineDelimiter)
+			if idx >= 0 && (remainingSpace-int64(idx)-1) >= 0 {
+				// We have space so write it to buffer
+				nw, err = f.writeToBuffer(p[n : n+idx+1])
+			} else if idx >= 0 {
+				// We found a new line but don't have space so just force rotate
+				forceRotate = true
+			} else if remainingToWrite > f.FileSize || f.FileSize-lineScanLimit < 0 {
+				// There is no new line remaining but there is no point in
+				// rotating since the remaining data will not even fit in the
+				// next file either so just fill this one up.
+				li := int64(n) + remainingSpace
+				if remainingSpace > remainingToWrite {
+					li = int64(n) + remainingToWrite
+				}
+				nw, err = f.writeToBuffer(p[n:li])
+			} else {
+				// There is no new line in the data remaining for us to write
+				// and it will fit in the next file so rotate.
+				forceRotate = true
+			}
 		} else {
 			// Write all the bytes in the current file
 			nw, err = f.writeToBuffer(p[n:])
@@ -283,7 +320,7 @@ func (f *FileRotator) createOrResetBuffer() {
 	f.bufLock.Lock()
 	defer f.bufLock.Unlock()
 	if f.bufw == nil {
-		f.bufw = bufio.NewWriterSize(f.currentFile, bufSize)
+		f.bufw = bufio.NewWriterSize(f.currentFile, logBufferSize)
 	} else {
 		f.bufw.Reset(f.currentFile)
 	}
diff --git a/client/driver/logging/rotator_test.go b/client/driver/logging/rotator_test.go
index 68b200e872e3..4fcf23952a0b 100644
--- a/client/driver/logging/rotator_test.go
+++ b/client/driver/logging/rotator_test.go
@@ -4,6 +4,7 @@ import (
 	"fmt"
 	"io/ioutil"
 	"log"
+	"math/rand"
 	"os"
 	"path/filepath"
 	"testing"
@@ -168,6 +169,65 @@ func TestFileRotator_RotateFiles(t *testing.T) {
 	})
 }
 
+func TestFileRotator_RotateFiles_Boundary(t *testing.T) {
+	t.Parallel()
+	var path string
+	var err error
+	if path, err = ioutil.TempDir("", pathPrefix); err != nil {
+		t.Fatalf("test setup err: %v", err)
+	}
+	defer os.RemoveAll(path)
+
+	fr, err := NewFileRotator(path, baseFileName, 10, 5, logger)
+	if err != nil {
+		t.Fatalf("test setup err: %v", err)
+	}
+
+	// We will write three times:
+	// 1st: Write with new lines spanning two files
+	// 2nd: Write long string with no new lines
+	// 3rd: Write a single new line
+	expectations := [][]byte{
+		[]byte("ab\n"),
+		[]byte("cdef\n"),
+		[]byte("12345"),
+		[]byte("67890"),
+		[]byte("\n"),
+	}
+
+	for _, str := range []string{"ab\ncdef\n", "1234567890", "\n"} {
+		nw, err := fr.Write([]byte(str))
+		if err != nil {
+			t.Fatalf("got error while writing: %v", err)
+		}
+
+		if nw != len(str) {
+			t.Fatalf("expected %v, got %v", len(str), nw)
+		}
+	}
+
+	var lastErr error
+	testutil.WaitForResult(func() (bool, error) {
+
+		for i, exp := range expectations {
+			fname := filepath.Join(path, fmt.Sprintf("redis.stdout.%d", i))
+			fi, err := os.Stat(fname)
+			if err != nil {
+				lastErr = err
+				return false, nil
+			}
+			if int(fi.Size()) != len(exp) {
+				lastErr = fmt.Errorf("expected size: %v, actual: %v", len(exp), fi.Size())
+				return false, nil
+			}
+		}
+
+		return true, nil
+	}, func(err error) {
+		t.Fatalf("%v", lastErr)
+	})
+}
+
 func TestFileRotator_WriteRemaining(t *testing.T) {
 	t.Parallel()
 	var path string
@@ -289,3 +349,48 @@ func TestFileRotator_PurgeOldFiles(t *testing.T) {
 		t.Fatalf("%v", lastErr)
 	})
 }
+
+func BenchmarkRotator(b *testing.B) {
+	kb := 1024
+	for _, inputSize := range []int{kb, 2 * kb, 4 * kb, 8 * kb, 16 * kb, 32 * kb, 64 * kb, 128 * kb, 256 * kb} {
+		b.Run(fmt.Sprintf("%dKB", inputSize/kb), func(b *testing.B) {
+			benchmarkRotatorWithInputSize(inputSize, b)
+		})
+	}
+}
+
+func benchmarkRotatorWithInputSize(size int, b *testing.B) {
+	var path string
+	var err error
+	if path, err = ioutil.TempDir("", pathPrefix); err != nil {
+		b.Fatalf("test setup err: %v", err)
+	}
+	defer os.RemoveAll(path)
+
+	fr, err := NewFileRotator(path, baseFileName, 5, 1024*1024, logger)
+	if err != nil {
+		b.Fatalf("test setup err: %v", err)
+	}
+	b.ResetTimer()
+
+	// run the Fib function b.N times
+	for n := 0; n < b.N; n++ {
+		// Generate some input
+		data := make([]byte, size)
+		_, err := rand.Read(data)
+		if err != nil {
+			b.Fatalf("Error generating date: %v", err)
+		}
+
+		// Insert random new lines
+		for i := 0; i < 100; i++ {
+			index := rand.Intn(size)
+			data[index] = '\n'
+		}
+
+		// Write the data
+		if _, err := fr.Write(data); err != nil {
+			b.Fatalf("Failed to write data: %v", err)
+		}
+	}
+}