diff --git a/wakatime/arguments.py b/wakatime/arguments.py
index 93ca291..34bd999 100644
--- a/wakatime/arguments.py
+++ b/wakatime/arguments.py
@@ -20,7 +20,7 @@ import traceback
 from .__about__ import __version__
 from .compat import basestring
 from .configs import parseConfigFile
-from .constants import AUTH_ERROR
+from .constants import AUTH_ERROR, DEFAULT_SYNC_OFFLINE_ACTIVITY
 from .packages import argparse
 
 
@@ -245,9 +245,9 @@ def parse_arguments():
             parser.error('argument --entity is required')
 
     if not args.sync_offline_activity:
-        args.sync_offline_activity = '5'
+        args.sync_offline_activity = DEFAULT_SYNC_OFFLINE_ACTIVITY
     if args.sync_offline_activity == 'none':
-        args.sync_offline_activity = '0'
+        args.sync_offline_activity = 0
     try:
         args.sync_offline_activity = int(args.sync_offline_activity)
         if args.sync_offline_activity < 0:
diff --git a/wakatime/constants.py b/wakatime/constants.py
index 0ee51be..938d673 100644
--- a/wakatime/constants.py
+++ b/wakatime/constants.py
@@ -45,3 +45,12 @@ Files larger than this in bytes will not have a line count stat for performance.
 Default is 2MB.
 """
 MAX_FILE_SIZE_SUPPORTED = 2000000
+
+""" Default number of offline heartbeats to sync before exiting."""
+DEFAULT_SYNC_OFFLINE_ACTIVITY = 100
+
+""" Number of heartbeats per api request.
+Even when sending more heartbeats, this is the number of heartbeats sent per
+individual https request to the WakaTime API.
+"""
+HEARTBEATS_PER_REQUEST = 10
diff --git a/wakatime/main.py b/wakatime/main.py
index dfd2b61..42c227e 100644
--- a/wakatime/main.py
+++ b/wakatime/main.py
@@ -24,7 +24,7 @@ from .__about__ import __version__
 from .api import send_heartbeats
 from .arguments import parse_arguments
 from .compat import u, json
-from .constants import SUCCESS, UNKNOWN_ERROR
+from .constants import SUCCESS, UNKNOWN_ERROR, HEARTBEATS_PER_REQUEST
 from .logger import setup_logging
 
 log = logging.getLogger('WakaTime')
@@ -63,11 +63,22 @@ def execute(argv=None):
                     msg=u(ex),
                 ))
 
-        retval = send_heartbeats(heartbeats, args, configs)
+        retval = SUCCESS
+        while heartbeats:
+            retval = send_heartbeats(heartbeats[:HEARTBEATS_PER_REQUEST], args, configs)
+            heartbeats = heartbeats[HEARTBEATS_PER_REQUEST:]
+            if retval != SUCCESS:
+                break
+
+        if heartbeats:
+            Queue(args, configs).push_many(heartbeats)
+
         if retval == SUCCESS:
             queue = Queue(args, configs)
             for offline_heartbeats in queue.pop_many(args.sync_offline_activity):
                 retval = send_heartbeats(offline_heartbeats, args, configs)
+                if retval != SUCCESS:
+                    break
 
         return retval
 
diff --git a/wakatime/offlinequeue.py b/wakatime/offlinequeue.py
index 94318e1..319f0d4 100644
--- a/wakatime/offlinequeue.py
+++ b/wakatime/offlinequeue.py
@@ -15,6 +15,7 @@ import os
 from time import sleep
 
 from .compat import json
+from .constants import DEFAULT_SYNC_OFFLINE_ACTIVITY, HEARTBEATS_PER_REQUEST
 from .heartbeat import Heartbeat
 
 
@@ -104,7 +105,7 @@ class Queue(object):
 
     def pop_many(self, limit=None):
         if limit is None:
-            limit = 5
+            limit = DEFAULT_SYNC_OFFLINE_ACTIVITY
 
         heartbeats = []
 
@@ -115,7 +116,7 @@ class Queue(object):
                 break
             heartbeats.append(heartbeat)
             count += 1
-            if count % 10 == 0:
+            if count % HEARTBEATS_PER_REQUEST == 0:
                 yield heartbeats
                 heartbeats = []