diff --git a/app/Http/Controllers/BillController.php b/app/Http/Controllers/BillController.php
index fc0e907480..aef8266959 100644
--- a/app/Http/Controllers/BillController.php
+++ b/app/Http/Controllers/BillController.php
@@ -137,7 +137,7 @@ class BillController extends Controller
         $bills = $repository->getBills();
         $bills->each(
             function (Bill $bill) use ($repository, $start, $end) {
-                $bill->nextExpectedMatch = $repository->nextExpectedMatch($bill);
+                $bill->nextExpectedMatch = $repository->nextExpectedMatch($bill, new Carbon);
                 $bill->lastFoundMatch    = $repository->lastFoundMatch($bill);
                 $journals                = $repository->getJournalsInRange($bill, $start, $end);
                 // loop journals, find average:
@@ -204,7 +204,7 @@ class BillController extends Controller
         $yearAverage    = $repository->getYearAverage($bill, $date);
         $overallAverage = $repository->getOverallAverage($bill);
         $journals->setPath('/bills/show/' . $bill->id);
-        $bill->nextExpectedMatch = $repository->nextExpectedMatch($bill);
+        $bill->nextExpectedMatch = $repository->nextExpectedMatch($bill, new Carbon);
         $hideBill                = true;
         $subTitle                = e($bill->name);
 
diff --git a/app/Repositories/Bill/BillRepository.php b/app/Repositories/Bill/BillRepository.php
index 2e12076d10..62000b620f 100644
--- a/app/Repositories/Bill/BillRepository.php
+++ b/app/Repositories/Bill/BillRepository.php
@@ -18,10 +18,12 @@ use DB;
 use FireflyIII\Models\Bill;
 use FireflyIII\Models\TransactionJournal;
 use FireflyIII\Models\TransactionType;
+use FireflyIII\Support\CacheProperties;
 use FireflyIII\User;
 use Illuminate\Database\Query\JoinClause;
 use Illuminate\Pagination\LengthAwarePaginator;
 use Illuminate\Support\Collection;
+use Log;
 use Navigation;
 
 /**
@@ -461,52 +463,44 @@ class BillRepository implements BillRepositoryInterface
     }
 
     /**
-     * @param Bill $bill
+     * @param Bill   $bill
+     * @param Carbon $date
      *
-     * @return \Carbon\Carbon
+     * @return Carbon
      */
-    public function nextExpectedMatch(Bill $bill): Carbon
+    public function nextExpectedMatch(Bill $bill, Carbon $date): Carbon
     {
-
-        $finalDate       = Carbon::now();
-        $finalDate->year = 1900;
-        if ($bill->active == 0) {
-            return $finalDate;
+        $cache = new CacheProperties;
+        $cache->addProperty($bill->id);
+        $cache->addProperty('nextExpectedMatch');
+        if ($cache->has()) {
+            return $cache->get();
         }
+        // find the most recent date for this bill NOT in the future. Cache this date:
+        $start = clone $bill->date;
+        $now   = new Carbon;
+        Log::debug('Start is ' . $start->format('Y-m-d'));
 
-        /*
-         * $today is the start of the next period, to make sure FF3 won't miss anything
-         * when the current period has a transaction journal.
-         */
-        /** @var \Carbon\Carbon $obj */
-        $obj   = new Carbon;
-        $today = Navigation::addPeriod($obj, $bill->repeat_freq, 0);
+        do {
+            $start = Navigation::addPeriod($start, $bill->repeat_freq, $bill->skip);
+            Log::debug('Start is now ' . $start->format('Y-m-d'));
+        } while ($start <= $now);
 
-        $skip  = $bill->skip + 1;
-        $start = Navigation::startOfPeriod($obj, $bill->repeat_freq);
-        /*
-         * go back exactly one month/week/etc because FF3 does not care about 'next'
-         * bills if they're too far into the past.
-         */
+        $end = Navigation::addPeriod($start, $bill->repeat_freq, $bill->skip);
+        Log::debug('Final start is ' . $start->format('Y-m-d'));
+        Log::debug('Matching end is ' . $end->format('Y-m-d'));
 
-        $counter = 0;
-        while ($start <= $today) {
-            if (($counter % $skip) == 0) {
-                // do something.
-                $end          = Navigation::endOfPeriod(clone $start, $bill->repeat_freq);
-                $journalCount = $bill->transactionJournals()->before($end)->after($start)->count();
-                if ($journalCount == 0) {
-                    $finalDate = new Carbon($start->format('Y-m-d'));
-                    break;
-                }
-            }
+        // see if the bill was paid in this period.
+        $journalCount = $bill->transactionJournals()->before($end)->after($start)->count();
 
-            // add period for next round!
-            $start = Navigation::addPeriod($start, $bill->repeat_freq, 0);
-            $counter++;
+        if ($journalCount > 0) {
+            // this period had in fact a bill. The new start is the current end, and we create a new end.
+            $start = clone $end;
+            $end   = Navigation::addPeriod($start, $bill->repeat_freq, $bill->skip);
         }
+        $cache->store($start);
 
-        return $finalDate;
+        return $start;
     }
 
     /**
diff --git a/app/Repositories/Bill/BillRepositoryInterface.php b/app/Repositories/Bill/BillRepositoryInterface.php
index f740921cec..195df50889 100644
--- a/app/Repositories/Bill/BillRepositoryInterface.php
+++ b/app/Repositories/Bill/BillRepositoryInterface.php
@@ -168,11 +168,12 @@ interface BillRepositoryInterface
 
 
     /**
-     * @param Bill $bill
+     * @param Bill   $bill
+     * @param Carbon $date
      *
      * @return \Carbon\Carbon
      */
-    public function nextExpectedMatch(Bill $bill): Carbon;
+    public function nextExpectedMatch(Bill $bill, Carbon $date): Carbon;
 
     /**
      * @param Bill               $bill
diff --git a/resources/views/list/bills.twig b/resources/views/list/bills.twig
index 380878a14e..1f2a8a51f7 100644
--- a/resources/views/list/bills.twig
+++ b/resources/views/list/bills.twig
@@ -6,7 +6,7 @@
         <th class="hidden-sm hidden-xs">{{ trans('list.matchesOn') }}</th>
         <th colspan="2">{{ trans('list.matchingAmount') }}</th>
         <th class="hidden-sm hidden-xs">{{ trans('list.paid_current_period') }}</th>
-        <th class="hidden-sm hidden-xs">{{ trans('list.expectedMatch') }}</th>
+        <th class="hidden-sm hidden-xs">{{ trans('list.next_expected_match') }}</th>
         <th class="hidden-sm hidden-xs">{{ trans('list.active') }}</th>
         <th class="hidden-sm hidden-xs">{{ trans('list.automatch') }}</th>
         <th class="hidden-sm hidden-xs">{{ trans('list.repeat_freq') }}</th>
diff --git a/storage/database/seed.bill-test.json b/storage/database/seed.bill-test.json
new file mode 100644
index 0000000000..857a357951
--- /dev/null
+++ b/storage/database/seed.bill-test.json
@@ -0,0 +1,84 @@
+{
+  "users": [
+    {
+      "email": "thegrumpydictator@gmail.com",
+      "password": "james"
+    },
+    {
+      "email": "thegrumpydictator+empty@gmail.com",
+      "password": "james"
+    },
+    {
+      "email": "thegrumpydictator+deleteme@gmail.com",
+      "password": "james"
+    }
+  ],
+  "roles": [
+    {
+      "user_id": 1,
+      "role": 1
+    }
+  ],
+  "accounts": [
+    {
+      "user_id": 1,
+      "account_type_id": 3,
+      "name": "Checking Account",
+      "iban": "NL11XOLA6707795988"
+    }
+  ],
+  "account-meta": [
+  ],
+  "bills": [
+    {
+      "name": "Some weird weekly bill",
+      "match": "weird,weekly,bill",
+      "amount_min": 30,
+      "amount_max": 35,
+      "user_id": 1,
+      "date": "2016-06-12",
+      "active": 1,
+      "automatch": 1,
+      "repeat_freq": "weekly",
+      "skip": 0
+    }
+  ],
+  "budgets": [
+  ],
+  "budget-limits": [
+  ],
+  "monthly-limits": [
+  ],
+  "categories": [
+  ],
+  "piggy-banks": [
+  ],
+  "piggy-events": [
+  ],
+  "rule-groups": [
+  ],
+  "rules": [
+  ],
+  "rule-triggers": [
+  ],
+  "rule-actions": [
+  ],
+  "tags": [
+  ],
+  "monthly-deposits": [
+  ],
+  "monthly-transfers": [
+  ],
+  "monthly-withdrawals": [
+  ],
+  "attachments": [
+  ],
+  "multi-withdrawals": [
+  ],
+  "multi-deposits": [
+  ],
+  "multi-transfers": [
+  ],
+  "import-jobs": [],
+  "currencies": []
+}
\ No newline at end of file
diff --git a/storage/database/seed.testing.json b/storage/database/seed.testing.json
index 847832ee07..d6f9dfe2ea 100644
--- a/storage/database/seed.testing.json
+++ b/storage/database/seed.testing.json
@@ -245,27 +245,15 @@
   ],
   "bills": [
     {
-      "name": "Rent",
-      "match": "rent,land,lord",
-      "amount_min": 795,
-      "amount_max": 805,
+      "name": "Some weird weekly bill",
+      "match": "weird,weekly,bill",
+      "amount_min": 30,
+      "amount_max": 35,
       "user_id": 1,
-      "date": "2015-01-01",
+      "date": "2016-06-12",
       "active": 1,
       "automatch": 1,
-      "repeat_freq": "monthly",
-      "skip": 0
-    },
-    {
-      "name": "Health insurance",
-      "match": "insurer,insurance,health",
-      "amount_min": 120,
-      "amount_max": 140,
-      "user_id": 1,
-      "date": "2015-01-01",
-      "active": 1,
-      "automatch": 1,
-      "repeat_freq": "monthly",
+      "repeat_freq": "weekly",
       "skip": 0
     }
   ],