diff --git a/CHANGELOG.md b/CHANGELOG.md
index 79da341..5cc955c 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -17,6 +17,7 @@ and this project adheres to [Semantic Versioning](https://semver.org/spec/v2.0.0
 - Handle cases where non-legacy puzzles don't have an `author` attribute
 - Handle YAML-formatted file and script lists as expected
 - YAML-formatted example puzzle actually works as expected
+- points.log will now always be sorted chronologically
 
 ## [3.4.3] - 2019-11-20
 ### Fixed
diff --git a/src/instance.go b/src/instance.go
index f446439..bdb9fdd 100644
--- a/src/instance.go
+++ b/src/instance.go
@@ -37,6 +37,7 @@ type Instance struct {
 	nextAttempt       map[string]time.Time
 	nextAttemptMutex  *sync.RWMutex
 	mux               *http.ServeMux
+	PointsMux         *sync.RWMutex
 }
 
 func (ctx *Instance) Initialize() error {
@@ -54,6 +55,7 @@ func (ctx *Instance) Initialize() error {
 	ctx.nextAttempt = map[string]time.Time{}
 	ctx.nextAttemptMutex = new(sync.RWMutex)
 	ctx.mux = http.NewServeMux()
+	ctx.PointsMux = new(sync.RWMutex)
 
 	ctx.BindHandlers()
 	ctx.MaybeInitialize()
@@ -83,7 +85,11 @@ func (ctx *Instance) MaybeInitialize() {
 	// Remove any extant control and state files
 	os.Remove(ctx.StatePath("until"))
 	os.Remove(ctx.StatePath("disabled"))
+
+	ctx.PointsMux.Lock()
 	os.Remove(ctx.StatePath("points.log"))
+	ctx.PointsMux.Unlock()
+
 	os.RemoveAll(ctx.StatePath("points.tmp"))
 	os.RemoveAll(ctx.StatePath("points.new"))
 	os.RemoveAll(ctx.StatePath("teams"))
@@ -156,6 +162,10 @@ func (ctx *Instance) PointsLog(teamId string) []*Award {
 	var ret []*Award
 
 	fn := ctx.StatePath("points.log")
+
+	ctx.PointsMux.RLock()
+	defer ctx.PointsMux.RUnlock()
+
 	f, err := os.Open(fn)
 	if err != nil {
 		log.Printf("Unable to open %s: %s", fn, err)
diff --git a/src/maintenance.go b/src/maintenance.go
index 0174902..65bb70e 100644
--- a/src/maintenance.go
+++ b/src/maintenance.go
@@ -4,9 +4,11 @@ import (
 	"bufio"
 	"encoding/json"
 	"fmt"
+	"io"
 	"io/ioutil"
 	"log"
 	"os"
+	"sort"
 	"strconv"
 	"strings"
 	"time"
@@ -95,7 +97,7 @@ func (ctx *Instance) generatePointsLog(teamId string) []byte {
 		log.Printf("Marshalling points.js: %v", err)
 		return nil
 	}
-	
+
 	if len(teamId) == 0 {
 		ctx.jPointsLog = jpl
 	}
@@ -203,6 +205,9 @@ func (ctx *Instance) readTeams() {
 // collectPoints gathers up files in points.new/ and appends their contents to points.log,
 // removing each points.new/ file as it goes.
 func (ctx *Instance) collectPoints() {
+	ctx.PointsMux.Lock()
+	defer ctx.PointsMux.Unlock()
+
 	logf, err := os.OpenFile(ctx.StatePath("points.log"), os.O_APPEND|os.O_CREATE|os.O_WRONLY, 0644)
 	if err != nil {
 		log.Printf("Can't append to points log: %s", err)
@@ -248,6 +253,46 @@ func (ctx *Instance) collectPoints() {
 	}
 }
 
+// Ensure that points.log is sorted chronologically
+func (ctx *Instance) sortPoints() {
+	var points []*Award
+
+	ctx.PointsMux.Lock()
+	defer ctx.PointsMux.Unlock()
+
+	logf, err := os.OpenFile(ctx.StatePath("points.log"), os.O_CREATE|os.O_RDWR, 0644)
+	if err != nil {
+		log.Printf("Can't sort points.log: %s", err)
+		return
+	}
+	defer logf.Close()
+
+	scanner := bufio.NewScanner(logf)
+	for scanner.Scan() {
+		line := scanner.Text()
+		cur, err := ParseAward(line)
+		if err != nil {
+			log.Printf("Encountered malformed award line, not sorting %s: %s", line, err)
+			return
+		}
+
+		points = append(points, cur)
+	}
+
+	// Only sort and write to file if we need to
+	if ! sort.SliceIsSorted(points, func( i, j int) bool { return points[i].When.Before(points[j].When) }) {
+
+		sort.SliceStable(points, func(i, j int) bool { return points[i].When.Before(points[j].When) })
+
+		logf.Seek(0, io.SeekStart)
+
+		for i := range points {
+			point := points[i]
+			fmt.Fprintf(logf, "%s\n", point.String())
+		}
+	}
+}
+
 func (ctx *Instance) isEnabled() bool {
 	// Skip if we've been disabled
 	if _, err := os.Stat(ctx.StatePath("disabled")); err == nil {
@@ -293,6 +338,7 @@ func (ctx *Instance) Maintenance(maintenanceInterval time.Duration) {
 			ctx.tidy()
 			ctx.readTeams()
 			ctx.collectPoints()
+			ctx.sortPoints()
 			ctx.generatePuzzleList()
 			ctx.generatePointsLog("")
 		}