diff --git a/lib/kubernetes-deploy/container_logs.rb b/lib/kubernetes-deploy/container_logs.rb
index 998bb3ec9..d43144d32 100644
--- a/lib/kubernetes-deploy/container_logs.rb
+++ b/lib/kubernetes-deploy/container_logs.rb
@@ -18,7 +18,7 @@ def initialize(parent_id:, container_name:, namespace:, context:, logger:)
     def sync
       new_logs = fetch_latest
       return unless new_logs.present?
-      @lines += deduplicate(new_logs)
+      @lines += sort_and_deduplicate(new_logs)
     end
 
     def empty?
@@ -60,18 +60,24 @@ def rfc3339_timestamp(time)
       time.strftime("%FT%T.%N%:z")
     end
 
-    def deduplicate(logs)
-      deduped = []
-      check_for_duplicate = true
+    def sort_and_deduplicate(logs)
+      parsed_lines = logs.map { |line| split_timestamped_line(line) }
+      sorted_lines = parsed_lines.sort do |(timestamp1, _msg1), (timestamp2, _msg2)|
+        if timestamp1.nil?
+          -1
+        elsif timestamp2.nil?
+          1
+        else
+          timestamp1 <=> timestamp2
+        end
+      end
 
-      logs.each do |line|
-        timestamp, msg = split_timestamped_line(line)
-        next if check_for_duplicate && likely_duplicate?(timestamp)
-        check_for_duplicate = false # logs are ordered, so once we've seen a new one, assume all subsequent logs are new
+      deduped = []
+      sorted_lines.each do |timestamp, msg|
+        next if likely_duplicate?(timestamp)
         @last_timestamp = timestamp if timestamp
         deduped << msg
       end
-
       deduped
     end
 
diff --git a/test/unit/container_logs_test.rb b/test/unit/container_logs_test.rb
index 33fceb3a3..f6342ef3b 100644
--- a/test/unit/container_logs_test.rb
+++ b/test/unit/container_logs_test.rb
@@ -81,8 +81,8 @@ def test_print_latest_supports_prefixing
   end
 
   def test_logs_without_timestamps_are_not_deduped
-    logs_response_1_with_anomaly = logs_response_1 + "Line 3.5"
-    logs_response_2_with_anomaly = "Line 3.5\n" + logs_response_2
+    logs_response_1_with_anomaly = logs_response_1 + "No timestamp"
+    logs_response_2_with_anomaly = "No timestamp 2\n" + logs_response_2
     KubernetesDeploy::Kubectl.any_instance.stubs(:run)
       .returns([logs_response_1_with_anomaly, "", ""])
       .then.returns([logs_response_2_with_anomaly, "", ""])
@@ -90,7 +90,14 @@ def test_logs_without_timestamps_are_not_deduped
     @logs.sync
     @logs.sync
     @logs.print_all
-    assert_logs_match("Line 3.5", 2)
+    assert_logs_match_all([
+      "No timestamp", # moved to start of batch 1
+      "Line 1",
+      "Line 2",
+      "Line 3",
+      "No timestamp 2", # moved to start of batch 2
+      "Line 4"
+    ], in_order: true)
   end
 
   def test_deduplication_works_when_exact_same_batch_is_returned_more_than_once
@@ -108,6 +115,43 @@ def test_deduplication_works_when_exact_same_batch_is_returned_more_than_once
     assert_logs_match("Line 2", 1)
   end
 
+  def test_deduplication_works_when_last_line_is_out_of_order
+    regression_data = <<~STRING
+      2018-12-13T12:17:23.727605598Z Line 1
+      2018-12-13T12:17:23.727696012Z Line 2
+      2018-12-13T12:17:23.728538913Z Line 3
+      2018-12-13T12:17:23.7287293Z Line 4
+      2018-12-13T12:17:23.729694842Z Line 5
+      2018-12-13T12:17:23.731259592Z Line 7
+      2018-12-13T12:17:23.73127007Z Line 8
+      2018-12-13T12:17:23.731273672Z Line 9
+      2018-12-13T12:17:23.731276862Z Line 10
+      2018-12-13T12:17:23.731284069Z Line 11
+      2018-12-13T12:17:23.731287054Z Line 12
+      2018-12-13T12:17:23.731289959Z Line 13
+      2018-12-13T12:17:23.731292814Z Line 14
+      2018-12-13T12:17:23.731295298Z Line 15
+      2018-12-13T12:17:23.731297747Z Line 16
+      2018-12-13T12:17:23.731297748Z Line 17
+      2018-12-13T12:17:23.729851532Z Line 6
+    STRING
+
+    KubernetesDeploy::Kubectl.any_instance.stubs(:run)
+      .returns([regression_data, "", ""]).times(12)
+
+    12.times do
+      @logs.sync
+      @logs.print_latest
+    end
+
+    expected_lines = generate_log_messages(1..17)
+
+    expected_lines.each do |line|
+      assert_logs_match(/#{line}$/, 1) # no duplicates
+    end
+    assert_logs_match_all(expected_lines, in_order: true) # sorted correctly
+  end
+
   private
 
   def generate_log_messages(range)