diff --git a/hledger-lib/Hledger/Data/Dates.hs b/hledger-lib/Hledger/Data/Dates.hs
index 20acae22e..7d5aa1d1a 100644
--- a/hledger-lib/Hledger/Data/Dates.hs
+++ b/hledger-lib/Hledger/Data/Dates.hs
@@ -63,6 +63,8 @@ module Hledger.Data.Dates (
   spanDefaultsFrom,
   spanUnion,
   spansUnion,
+  daysSpan,
+  latestSpanContaining,
   smartdate,
   splitSpan,
   fixSmartDate,
@@ -79,10 +81,11 @@ import Prelude ()
 import "base-compat-batteries" Prelude.Compat hiding (fail)
 import qualified "base-compat-batteries" Control.Monad.Fail.Compat as Fail (MonadFail, fail)
 import Control.Applicative.Permutations
-import Control.Monad (unless)
+import Control.Monad (guard, unless)
 import "base-compat-batteries" Data.List.Compat
 import Data.Default
 import Data.Maybe
+import qualified Data.Set as Set
 import Data.Text (Text)
 import qualified Data.Text as T
 #if MIN_VERSION_time(1,5,0)
@@ -95,7 +98,7 @@ import Data.Time.Calendar
 import Data.Time.Calendar.OrdinalDate
 import Data.Time.Clock
 import Data.Time.LocalTime
-import Safe (headMay, lastMay, readMay)
+import Safe (headMay, lastMay, readMay, maximumMay, minimumMay)
 import Text.Megaparsec
 import Text.Megaparsec.Char
 import Text.Megaparsec.Custom
@@ -231,9 +234,8 @@ daysInSpan _ = Nothing
 
 -- | Is this an empty span, ie closed with the end date on or before the start date ?
 isEmptySpan :: DateSpan -> Bool
-isEmptySpan s = case daysInSpan s of
-                  Just n  -> n < 1
-                  Nothing -> False
+isEmptySpan (DateSpan (Just s) (Just e)) = e <= s
+isEmptySpan _                            = False
 
 -- | Does the span include the given date ?
 spanContainsDate :: DateSpan -> Day -> Bool
@@ -287,6 +289,36 @@ earliest d Nothing = d
 earliest Nothing d = d
 earliest (Just d1) (Just d2) = Just $ min d1 d2
 
+-- | Calculate the minimal DateSpan containing all of the given Days (in the
+-- usual exclusive-end-date sense: beginning on the earliest, and ending on
+-- the day after the latest).
+daysSpan :: [Day] -> DateSpan
+daysSpan ds = DateSpan (minimumMay ds) (addDays 1 <$> maximumMay ds)
+
+-- | Select the DateSpan containing a given Day, if any, from a given list of
+-- DateSpans.
+--
+-- If the DateSpans are non-overlapping, this returns the unique containing
+-- DateSpan, if it exists. If the DateSpans are overlapping, it will return the
+-- containing DateSpan with the latest start date, and then latest end date.
+
+-- Note: This will currently return `DateSpan (Just s) (Just e)` before it will
+-- return `DateSpan (Just s) Nothing`. It's unclear which behaviour is desired.
+-- This is irrelevant at the moment as it's never applied to any list with
+-- overlapping DateSpans.
+latestSpanContaining :: [DateSpan] -> Day -> Maybe DateSpan
+latestSpanContaining datespans = go
+  where
+    go day = do
+        span <- Set.lookupLT supSpan spanSet
+        guard $ spanContainsDate span day
+        return span
+      where
+        -- The smallest DateSpan larger than any DateSpan containing day.
+        supSpan = DateSpan (Just $ addDays 1 day) Nothing
+
+    spanSet = Set.fromList $ filter (not . isEmptySpan) datespans
+
 -- | Parse a period expression to an Interval and overall DateSpan using
 -- the provided reference date, or return a parse error.
 parsePeriodExpr
diff --git a/hledger-lib/Hledger/Data/Ledger.hs b/hledger-lib/Hledger/Data/Ledger.hs
index 91fdcbae2..a0c3c7767 100644
--- a/hledger-lib/Hledger/Data/Ledger.hs
+++ b/hledger-lib/Hledger/Data/Ledger.hs
@@ -34,8 +34,9 @@ import Text.Printf
 import Hledger.Utils.Test
 import Hledger.Data.Types
 import Hledger.Data.Account
+import Hledger.Data.Dates (daysSpan)
 import Hledger.Data.Journal
-import Hledger.Data.Posting
+import Hledger.Data.Posting (postingDate)
 import Hledger.Query
 
 
@@ -100,7 +101,7 @@ ledgerPostings = journalPostings . ljournal
 -- | The (fully specified) date span containing all the ledger's (filtered) transactions,
 -- or DateSpan Nothing Nothing if there are none.
 ledgerDateSpan :: Ledger -> DateSpan
-ledgerDateSpan = postingsDateSpan . ledgerPostings
+ledgerDateSpan = daysSpan . map postingDate . ledgerPostings
 
 -- | All commodities used in this ledger.
 ledgerCommodities :: Ledger -> [CommoditySymbol]
diff --git a/hledger-lib/Hledger/Data/Posting.hs b/hledger-lib/Hledger/Data/Posting.hs
index bb330a749..67af366fc 100644
--- a/hledger-lib/Hledger/Data/Posting.hs
+++ b/hledger-lib/Hledger/Data/Posting.hs
@@ -42,8 +42,6 @@ module Hledger.Data.Posting (
   postingDate2,
   isPostingInDateSpan,
   isPostingInDateSpan',
-  postingsDateSpan,
-  postingsDateSpan',
   -- * account name operations
   accountNamesFromPostings,
   accountNamePostingType,
@@ -69,6 +67,8 @@ module Hledger.Data.Posting (
   tests_Posting
 )
 where
+
+import Data.Foldable (asum)
 import Data.List
 import qualified Data.Map as M
 import Data.Maybe
@@ -204,20 +204,19 @@ removePrices p = p{ pamount = Mixed $ remove <$> amounts (pamount p) }
 -- otherwise the parent transaction's primary date, or the null date if
 -- there is no parent transaction.
 postingDate :: Posting -> Day
-postingDate p = fromMaybe txndate $ pdate p
-    where
-      txndate = maybe nulldate tdate $ ptransaction p
+postingDate p = fromMaybe nulldate $ asum dates
+    where dates = [ pdate p, tdate <$> ptransaction p ]
 
 -- | Get a posting's secondary (secondary) date, which is the first of:
 -- posting's secondary date, transaction's secondary date, posting's
 -- primary date, transaction's primary date, or the null date if there is
 -- no parent transaction.
 postingDate2 :: Posting -> Day
-postingDate2 p = headDef nulldate $ catMaybes dates
-  where dates = [pdate2 p
-                ,maybe Nothing tdate2 $ ptransaction p
-                ,pdate p
-                ,fmap tdate (ptransaction p)
+postingDate2 p = fromMaybe nulldate $ asum dates
+  where dates = [ pdate2 p
+                , tdate2 =<< ptransaction p
+                , pdate p
+                , tdate <$> ptransaction p
                 ]
 
 -- | Get a posting's status. This is cleared or pending if those are
@@ -246,7 +245,7 @@ relatedPostings _ = []
 
 -- | Does this posting fall within the given date span ?
 isPostingInDateSpan :: DateSpan -> Posting -> Bool
-isPostingInDateSpan s = spanContainsDate s . postingDate
+isPostingInDateSpan = isPostingInDateSpan' PrimaryDate
 
 -- --date2-sensitive version, separate for now to avoid disturbing multiBalanceReport.
 isPostingInDateSpan' :: WhichDate -> DateSpan -> Posting -> Bool
@@ -256,21 +255,6 @@ isPostingInDateSpan' SecondaryDate s = spanContainsDate s . postingDate2
 isEmptyPosting :: Posting -> Bool
 isEmptyPosting = isZeroMixedAmount . pamount
 
--- | Get the minimal date span which contains all the postings, or the
--- null date span if there are none.
-postingsDateSpan :: [Posting] -> DateSpan
-postingsDateSpan [] = DateSpan Nothing Nothing
-postingsDateSpan ps = DateSpan (Just $ postingDate $ head ps') (Just $ addDays 1 $ postingDate $ last ps')
-    where ps' = sortOn postingDate ps
-
--- --date2-sensitive version, as above.
-postingsDateSpan' :: WhichDate -> [Posting] -> DateSpan
-postingsDateSpan' _  [] = DateSpan Nothing Nothing
-postingsDateSpan' wd ps = DateSpan (Just $ postingdate $ head ps') (Just $ addDays 1 $ postingdate $ last ps')
-    where
-      ps' = sortOn postingdate ps
-      postingdate = if wd == PrimaryDate then postingDate else postingDate2
-
 -- AccountName stuff that depends on PostingType
 
 accountNamePostingType :: AccountName -> PostingType
diff --git a/hledger-lib/Hledger/Reports/MultiBalanceReport.hs b/hledger-lib/Hledger/Reports/MultiBalanceReport.hs
index 54055a384..1daf85e81 100644
--- a/hledger-lib/Hledger/Reports/MultiBalanceReport.hs
+++ b/hledger-lib/Hledger/Reports/MultiBalanceReport.hs
@@ -24,6 +24,7 @@ where
 import GHC.Generics (Generic)
 import Control.DeepSeq (NFData)
 import Data.List
+import qualified Data.Map as M
 import Data.Maybe
 import Data.Ord
 import Data.Time.Calendar
@@ -150,7 +151,7 @@ multiBalanceReportWith ropts@ReportOpts{..} q j priceoracle =
           displayspan
             | empty_    = dbg1 "displayspan (-E)" reportspan                              -- all the requested intervals
             | otherwise = dbg1 "displayspan" $ requestedspan `spanIntersect` matchedspan  -- exclude leading/trailing empty intervals
-          matchedspan = dbg1 "matchedspan" $ postingsDateSpan' (whichDateFromOpts ropts) ps
+          matchedspan = dbg1 "matchedspan" . daysSpan $ map snd ps
 
       -- If doing cost valuation, convert amounts to cost.
       j' = journalSelectingAmountFromOpts ropts j
@@ -187,17 +188,26 @@ multiBalanceReportWith ropts@ReportOpts{..} q j priceoracle =
       -- 3. Gather postings for each column.
 
       -- Postings matching the query within the report period.
-      ps :: [Posting] =
+      ps :: [(Posting, Day)] =
           dbg1 "ps" $
+          map postingWithDate $
           journalPostings $
           filterJournalAmounts symq $      -- remove amount parts excluded by cur:
           filterJournalPostings reportq $  -- remove postings not matched by (adjusted) query
           j'
+        where
+          postingWithDate p = case whichDateFromOpts ropts of
+              PrimaryDate   -> (p, postingDate p)
+              SecondaryDate -> (p, postingDate2 p)
 
       -- Group postings into their columns, with the column end dates.
       colps :: [([Posting], Maybe Day)] =
           dbg1 "colps"
-          [(filter (isPostingInDateSpan' (whichDateFromOpts ropts) s) ps, spanEnd s) | s <- colspans]
+          [ (posts, end) | (DateSpan _ end, posts) <- M.toList colMap ]
+        where
+          colMap = foldr addPosting emptyMap ps
+          addPosting (p, d) = maybe id (M.adjust (p:)) $ latestSpanContaining colspans d
+          emptyMap = M.fromList . zip colspans $ repeat []
 
       ----------------------------------------------------------------------
       -- 4. Calculate account balance changes in each column.
@@ -228,13 +238,13 @@ multiBalanceReportWith ropts@ReportOpts{..} q j priceoracle =
           then nub $ sort $ startaccts ++ allpostedaccts
           else allpostedaccts
         where
-          allpostedaccts :: [AccountName] = dbg1 "allpostedaccts" $ sort $ accountNamesFromPostings ps
+          allpostedaccts :: [AccountName] =
+            dbg1 "allpostedaccts" . sort . accountNamesFromPostings $ map fst ps
       -- Each column's balance changes for each account, adding zeroes where needed.
       colallacctchanges :: [[(ClippedAccountName, MixedAmount)]] =
           dbg1 "colallacctchanges"
-          [sortBy (comparing fst) $
-           unionBy (\(a,_) (a',_) -> a == a') postedacctchanges zeroes
-           | postedacctchanges <- colacctchanges]
+          [ sortOn fst $ unionBy (\(a,_) (a',_) -> a == a') postedacctchanges zeroes
+             | postedacctchanges <- colacctchanges ]
           where zeroes = [(a, nullmixedamt) | a <- displayaccts]
       -- Transpose to get each account's balance changes across all columns.
       acctchanges :: [(ClippedAccountName, [MixedAmount])] =