diff --git a/cardano-chain-gen/test/Test/Cardano/Db/Mock/Unit/Conway.hs b/cardano-chain-gen/test/Test/Cardano/Db/Mock/Unit/Conway.hs
index 7ae03a9f7..b7a753d3e 100644
--- a/cardano-chain-gen/test/Test/Cardano/Db/Mock/Unit/Conway.hs
+++ b/cardano-chain-gen/test/Test/Cardano/Db/Mock/Unit/Conway.hs
@@ -118,6 +118,7 @@ unitTests iom knownMigrations =
     , testGroup
         "rollbacks"
         [ test "simple rollback" Rollback.simpleRollback
+        , test "drepDistr rollback" Rollback.drepDistrRollback
         , test "sync bigger chain" Rollback.bigChain
         , test "rollback while db-sync is off" Rollback.restartAndRollback
         , test "big rollback executed lazily" Rollback.lazyRollback
diff --git a/cardano-chain-gen/test/Test/Cardano/Db/Mock/Unit/Conway/Rollback.hs b/cardano-chain-gen/test/Test/Cardano/Db/Mock/Unit/Conway/Rollback.hs
index 0a524e99b..27176412b 100644
--- a/cardano-chain-gen/test/Test/Cardano/Db/Mock/Unit/Conway/Rollback.hs
+++ b/cardano-chain-gen/test/Test/Cardano/Db/Mock/Unit/Conway/Rollback.hs
@@ -1,4 +1,5 @@
 {-# LANGUAGE NumericUnderscores #-}
+{-# OPTIONS_GHC -Wno-x-partial #-}
 
 module Test.Cardano.Db.Mock.Unit.Conway.Rollback (
   simpleRollback,
@@ -10,14 +11,18 @@ module Test.Cardano.Db.Mock.Unit.Conway.Rollback (
   stakeAddressRollback,
   rollbackChangeTxOrder,
   rollbackFullTx,
+  drepDistrRollback,
 ) where
 
+import qualified Cardano.Db as DB
+import Cardano.DbSync.Era.Shelley.Generic.Util (unCredentialHash)
 import Cardano.Ledger.Coin (Coin (..))
 import Cardano.Ledger.Conway.TxCert (ConwayDelegCert (..), Delegatee (..))
 import Cardano.Mock.ChainSync.Server (IOManager (), addBlock, rollback)
 import Cardano.Mock.Forging.Interpreter (forgeNext)
 import qualified Cardano.Mock.Forging.Tx.Conway as Conway
 import Cardano.Mock.Forging.Tx.Generic (resolvePool)
+import qualified Cardano.Mock.Forging.Tx.Generic as Forging
 import Cardano.Mock.Forging.Types (PoolIndex (..), StakeIndex (..), UTxOIndex (..))
 import Cardano.Prelude
 import Data.Maybe.Strict (StrictMaybe (..))
@@ -25,9 +30,9 @@ import Ouroboros.Network.Block (blockPoint)
 import Test.Cardano.Db.Mock.Config
 import Test.Cardano.Db.Mock.Examples (mockBlock0, mockBlock1, mockBlock2)
 import Test.Cardano.Db.Mock.UnifiedApi
-import Test.Cardano.Db.Mock.Validate (assertBlockNoBackoff, assertTxCount)
+import Test.Cardano.Db.Mock.Validate (assertBlockNoBackoff, assertEqQuery, assertTxCount)
 import Test.Tasty.HUnit (Assertion ())
-import Prelude (last)
+import Prelude (error, head, last)
 
 simpleRollback :: IOManager -> [(Text, Text)] -> Assertion
 simpleRollback =
@@ -55,7 +60,7 @@ simpleRollback =
 
 bigChain :: IOManager -> [(Text, Text)] -> Assertion
 bigChain =
-  withFullConfig conwayConfigDir testLabel $ \interpreter mockServer dbSync -> do
+  withFullConfigDropDB conwayConfigDir testLabel $ \interpreter mockServer dbSync -> do
     -- Forge some blocks
     forM_ (replicate 101 mockBlock0) (forgeNextAndSubmit interpreter mockServer)
 
@@ -81,7 +86,7 @@ bigChain =
 
 restartAndRollback :: IOManager -> [(Text, Text)] -> Assertion
 restartAndRollback =
-  withFullConfig conwayConfigDir testLabel $ \interpreter mockServer dbSync -> do
+  withFullConfigDropDB conwayConfigDir testLabel $ \interpreter mockServer dbSync -> do
     -- Forge some blocks
     forM_ (replicate 101 mockBlock0) (forgeNextAndSubmit interpreter mockServer)
 
@@ -109,7 +114,7 @@ restartAndRollback =
 
 lazyRollback :: IOManager -> [(Text, Text)] -> Assertion
 lazyRollback =
-  withFullConfig conwayConfigDir testLabel $ \interpreter mockServer dbSync -> do
+  withFullConfigDropDB conwayConfigDir testLabel $ \interpreter mockServer dbSync -> do
     startDBSync dbSync
 
     -- Create a point to rollback to
@@ -134,7 +139,7 @@ lazyRollback =
 
 lazyRollbackRestart :: IOManager -> [(Text, Text)] -> Assertion
 lazyRollbackRestart =
-  withFullConfig conwayConfigDir testLabel $ \interpreter mockServer dbSync -> do
+  withFullConfigDropDB conwayConfigDir testLabel $ \interpreter mockServer dbSync -> do
     startDBSync dbSync
 
     -- Create a point to rollback to
@@ -162,7 +167,7 @@ lazyRollbackRestart =
 
 doubleRollback :: IOManager -> [(Text, Text)] -> Assertion
 doubleRollback =
-  withFullConfig conwayConfigDir testLabel $ \interpreter mockServer dbSync -> do
+  withFullConfigDropDB conwayConfigDir testLabel $ \interpreter mockServer dbSync -> do
     startDBSync dbSync
 
     -- Create points to rollback to
@@ -197,7 +202,7 @@ doubleRollback =
 
 stakeAddressRollback :: IOManager -> [(Text, Text)] -> Assertion
 stakeAddressRollback =
-  withFullConfig conwayConfigDir testLabel $ \interpreter mockServer dbSync -> do
+  withFullConfigDropDB conwayConfigDir testLabel $ \interpreter mockServer dbSync -> do
     startDBSync dbSync
 
     -- Create a point to rollbackTo
@@ -231,7 +236,7 @@ stakeAddressRollback =
 
 rollbackChangeTxOrder :: IOManager -> [(Text, Text)] -> Assertion
 rollbackChangeTxOrder =
-  withFullConfig conwayConfigDir testLabel $ \interpreter mockServer dbSync -> do
+  withFullConfigDropDB conwayConfigDir testLabel $ \interpreter mockServer dbSync -> do
     startDBSync dbSync
 
     -- Create a point to rollback to
@@ -262,7 +267,7 @@ rollbackChangeTxOrder =
 
 rollbackFullTx :: IOManager -> [(Text, Text)] -> Assertion
 rollbackFullTx =
-  withFullConfig conwayConfigDir testLabel $ \interpreter mockServer dbSync -> do
+  withFullConfigDropDB conwayConfigDir testLabel $ \interpreter mockServer dbSync -> do
     startDBSync dbSync
 
     -- Create a point to rollback to
@@ -291,3 +296,76 @@ rollbackFullTx =
     assertTxCount dbSync 14
   where
     testLabel = "conwayRollbackFullTx"
+
+-- | Test for DrepDistr rollback edge case when rolling back to an epoch boundary.
+-- Verifies that DrepDistr records are properly deleted during rollback and replay succeeds
+-- without duplicate key constraint violations.
+drepDistrRollback :: IOManager -> [(Text, Text)] -> Assertion
+drepDistrRollback =
+  withFullConfigDropDB conwayConfigDir testLabel $ \interpreter mockServer dbSync -> do
+    startDBSync dbSync
+
+    -- Register stake credentials and DReps
+    void $ registerAllStakeCreds interpreter mockServer
+    void $ registerDRepsAndDelegateVotes interpreter mockServer
+
+    -- Fill the rest of epoch 0 and cross into epoch 1
+    -- This triggers insertDrepDistr for epoch 1 at the epoch boundary (first block of epoch 1)
+    epoch0 <- fillUntilNextEpoch interpreter mockServer
+    assertBlockNoBackoff dbSync (2 + length epoch0)
+
+    -- Verify DrepDistr for epoch 1 was inserted
+    let drepId = Prelude.head Forging.unregisteredDRepIds
+    assertEqQuery
+      dbSync
+      (DB.queryDRepDistrAmount (unCredentialHash drepId) 1)
+      10_000
+      "Expected DrepDistr for epoch 1 after crossing boundary"
+
+    -- Fill all of epoch 1 and cross into epoch 2
+    epoch1 <- fillUntilNextEpoch interpreter mockServer
+    assertBlockNoBackoff dbSync (2 + length epoch0 + length epoch1)
+
+    -- Verify DrepDistr for epoch 2 was inserted
+    assertEqQuery
+      dbSync
+      (DB.queryDRepDistrAmount (unCredentialHash drepId) 2)
+      10_000
+      "Expected DrepDistr for epoch 2 after crossing boundary"
+
+    -- Identify the epoch 2 boundary block (last block of epoch1 list)
+    rollbackPoint <- case reverse epoch1 of
+      [] -> error "fillUntilNextEpoch returned empty list for epoch 1"
+      (epoch2Boundary : _) -> pure $ blockPoint epoch2Boundary
+
+    -- Continue a bit into epoch 2 (after DrepDistr insertion at the boundary)
+    blksAfter <- forgeAndSubmitBlocks interpreter mockServer 3
+    assertBlockNoBackoff dbSync (2 + length epoch0 + length epoch1 + length blksAfter)
+
+    -- Rollback to the epoch 2 boundary (first block of epoch 2)
+    rollbackTo interpreter mockServer rollbackPoint
+
+    -- Create fork - replay through the epoch 2 boundary
+    -- This will re-insert DrepDistr for epoch 2
+    -- SUCCESS: No duplicate key constraint violation because epoch 2 was properly deleted
+    -- (If the fix didn't work, we'd get a unique constraint violation here)
+    blksFork <- forgeAndSubmitBlocks interpreter mockServer 5
+
+    -- Verify DrepDistr for epoch 1 still exists (not affected by rollback)
+    assertEqQuery
+      dbSync
+      (DB.queryDRepDistrAmount (unCredentialHash drepId) 1)
+      10_000
+      "DrepDistr for epoch 1 should still exist after rollback"
+
+    -- Verify final state
+    assertBlockNoBackoff dbSync (2 + length epoch0 + length epoch1 + length blksFork)
+
+    -- Verify DrepDistr for both epochs exist after replay
+    assertEqQuery
+      dbSync
+      (DB.queryDRepDistrAmount (unCredentialHash drepId) 2)
+      10_000
+      "DrepDistr for epoch 2 should be re-inserted after replay through boundary"
+  where
+    testLabel = "conwayDrepDistrRollback"
diff --git a/cardano-chain-gen/test/testfiles/fingerprint/conwayDrepDistrRollback b/cardano-chain-gen/test/testfiles/fingerprint/conwayDrepDistrRollback
new file mode 100644
index 000000000..b1a9e7690
--- /dev/null
+++ b/cardano-chain-gen/test/testfiles/fingerprint/conwayDrepDistrRollback
@@ -0,0 +1 @@
+[12,16,18,21,24,30,31,32,33,40,41,42,43,47,52,60,62,70,80,84,86,92,98,100,106,109,110,111,112,127,134,138,146,149,154,166,168,178,183,188,193,194,198,200,202,220,222,223,224,225,231,239,242,247,261,282,283,288,289,301,302,303,308,313,315,316,320,331,334,344,345,363,364,368,369,375,377,381,389,394,407,418,422,425,430,437,438,439,440,447,450,453,454,456,458,461,467,492,499,507,516,524,538,541,544,546,550,567,573,576,577,579,580,586,589,595,597,603,605,609,616,618,619,623,624,634,636,643,644,659,664,665,672,678,692,705,711,712,719,726,730,739,740,743,747,749,751,754,759,762,763,765,767,773,777,786,788,789,794,801,806,807,829,830,832,849,851,853,869,871,874,875,878,882,888,893,895,896,898,899,903,906,908,911,912,913,922,930,932,938,941,944,950,960,963,966,968,972,977,985,986,988,990,991,994,997,1001,1005,1008,1014,1005,1008,1014,1019,1020]
\ No newline at end of file
diff --git a/cardano-chain-gen/test/testfiles/pgpass-testing-macos b/cardano-chain-gen/test/testfiles/pgpass-testing-macos
new file mode 100644
index 000000000..c3e830cab
--- /dev/null
+++ b/cardano-chain-gen/test/testfiles/pgpass-testing-macos
@@ -0,0 +1 @@
+/tmp:5432:testing:*:*
diff --git a/cardano-db-sync/src/Cardano/DbSync/Era/Universal/Insert/LedgerEvent.hs b/cardano-db-sync/src/Cardano/DbSync/Era/Universal/Insert/LedgerEvent.hs
index 9d873a5ea..e0e5c0cf8 100644
--- a/cardano-db-sync/src/Cardano/DbSync/Era/Universal/Insert/LedgerEvent.hs
+++ b/cardano-db-sync/src/Cardano/DbSync/Era/Universal/Insert/LedgerEvent.hs
@@ -18,7 +18,7 @@ import Cardano.Prelude
 import Cardano.Slotting.Slot (EpochNo (..))
 
 import Cardano.DbSync.Api
-import Cardano.DbSync.Api.Types (EpochStatistics (..), SyncEnv (..), InsertOptions (..), UnicodeNullSource, formatUnicodeNullSource)
+import Cardano.DbSync.Api.Types (EpochStatistics (..), InsertOptions (..), SyncEnv (..), UnicodeNullSource, formatUnicodeNullSource)
 import Cardano.DbSync.Cache.Types (textShowCacheStats)
 import Cardano.DbSync.Era.Cardano.Util (insertEpochSyncTime, resetEpochStatistics)
 import qualified Cardano.DbSync.Era.Shelley.Generic as Generic
@@ -54,7 +54,7 @@ insertNewEpochLedgerEvents syncEnv currentEpochNo@(EpochNo curEpoch) =
     tracer = getTrace syncEnv
     cache = envCache syncEnv
     ntw = getNetwork syncEnv
-    iopts = getInsertOptions syncEnv
+    iopts = getInsertOptions syncEnv
 
     subFromCurrentEpoch :: Word64 -> EpochNo
     subFromCurrentEpoch m =
diff --git a/cardano-db/src/Cardano/Db/Statement/Base.hs b/cardano-db/src/Cardano/Db/Statement/Base.hs
index 5417fd7bd..ae0d6fa79 100644
--- a/cardano-db/src/Cardano/Db/Statement/Base.hs
+++ b/cardano-db/src/Cardano/Db/Statement/Base.hs
@@ -187,12 +187,18 @@ queryBlockNoAndEpochStmt =
       epochNo <- HsqlD.column (HsqlD.nonNullable $ fromIntegral <$> HsqlD.int8)
       pure (blockId, epochNo)
 
+    -- Get the block ID of the rollback point, but the epoch_no of the previous block.
+    -- This handles the edge case where rollback is to the first block of a new epoch
+    -- (where DrepDistr will be inserted). Using the previous block's epoch ensures
+    -- DrepDistr for the current epoch gets deleted, preventing duplicates
+    -- when replaying through the epoch boundary.
     sql =
       TextEnc.encodeUtf8 $
         Text.concat
-          [ "SELECT id, epoch_no"
-          , " FROM " <> tableName (Proxy @a)
-          , " WHERE block_no = $1"
+          [ "SELECT curr.id, prev.epoch_no"
+          , " FROM " <> tableName (Proxy @a) <> " curr"
+          , " JOIN " <> tableName (Proxy @a) <> " prev ON prev.block_no = $1 - 1"
+          , " WHERE curr.block_no = $1"
           ]
 
 queryBlockNoAndEpoch :: Word64 -> DbM (Maybe (Id.BlockId, Word64))
@@ -686,6 +692,9 @@ deleteBlocksBlockId ::
 deleteBlocksBlockId trce txOutVariantType blockId epochN isConsumedTxOut = do
   let rb = "Rollback - "
 
+  -- Log the epoch being used (comes from previous block's epoch for epoch boundary rollbacks)
+  liftIO $ logInfo trce $ rb <> "Using epoch " <> textShow epochN <> " (from previous block) for epoch-related deletions"
+
   withProgress (Just trce) 6 rb $ \progressRef -> do
     -- Step 0: Initialize
     liftIO $ updateProgress (Just trce) progressRef 0 (rb <> "Initializing rollback...")
@@ -781,6 +790,9 @@ deleteUsingEpochNo trce epochN = do
   let epochEncoder = fromIntegral >$< HsqlE.param (HsqlE.nonNullable HsqlE.int8)
       epochInt64 = fromIntegral epochN
 
+  -- Log which epoch is being used for deletion (this comes from previous block's epoch for boundary rollbacks)
+  liftIO $ logInfo trce $ "Rollback - Using epoch " <> textShow epochN <> " for deletion (DrepDistr: epoch_no > " <> textShow epochN <> ")"
+
   -- First, count what we're about to delete for progress tracking
   totalCounts <- withProgress (Just trce) 5 "Counting epoch records..." $ \progressRef -> do
     liftIO $ updateProgress (Just trce) progressRef 0 "Counting Epoch records..."
@@ -788,6 +800,7 @@ deleteUsingEpochNo trce epochN = do
 
     liftIO $ updateProgress (Just trce) progressRef 1 "Counting DrepDistr records..."
     dc <- runSession mkDbCallStack $ HsqlSes.statement epochN (parameterisedCountWhere @SC.DrepDistr "epoch_no" "> $1" epochEncoder)
+    liftIO $ logInfo trce $ "Rollback - Found " <> textShow dc <> " DrepDistr records to delete for epochs > " <> textShow epochN
 
     liftIO $ updateProgress (Just trce) progressRef 2 "Counting RewardRest records..."
     rrc <- runSession mkDbCallStack $ HsqlSes.statement epochN (parameterisedCountWhere @SC.RewardRest "spendable_epoch" "> $1" epochEncoder)
diff --git a/config/pgpass-mainnet-macos b/config/pgpass-mainnet-macos
new file mode 100644
index 000000000..bb4733a29
--- /dev/null
+++ b/config/pgpass-mainnet-macos
@@ -0,0 +1 @@
+/tmp:5432:cexplorer:*:*
diff --git a/scripts/run-everything-tmux.sh b/scripts/run-everything-tmux.sh
index d85138770..c6d845c24 100755
--- a/scripts/run-everything-tmux.sh
+++ b/scripts/run-everything-tmux.sh
@@ -27,8 +27,8 @@ tmux send-keys -t 0 "cardano-node run --config $TESTNET_DIR/config.json --databa
 
 # Cardano DB-Sync
 tmux send-keys -t 1 "cd $CARDANO_DB_SYNC_DIR/" 'C-m'; sleep 3
-tmux send-keys -t 1 "export PGPASSFILE=$CARDANO_DB_SYNC_DIR/config/pgpass-mainnet" 'C-m'; sleep 2
-tmux send-keys -t 1 "PGPASSFILE=$CARDANO_DB_SYNC_DIR/config/pgpass-mainnet $dbsync --config $TESTNET_DIR/db-sync-config.json --socket-path $TESTNET_DIR/db/node.socket --state-dir $TESTNET_DIR/ledger-state --schema-dir $CARDANO_DB_SYNC_DIR/schema/" 'C-m'
+tmux send-keys -t 1 "export PGPASSFILE=$CARDANO_DB_SYNC_DIR/config/pgpass-mainnet-macos" 'C-m'; sleep 2
+tmux send-keys -t 1 "PGPASSFILE=$CARDANO_DB_SYNC_DIR/config/pgpass-mainnet-macos $dbsync --config $TESTNET_DIR/db-sync-config.json --socket-path $TESTNET_DIR/db/node.socket --state-dir $TESTNET_DIR/ledger-state --schema-dir $CARDANO_DB_SYNC_DIR/schema/" 'C-m'
 # tmux send-keys -t 1 "$dbsync --config $TESTNET_DIR/db-sync-config.json --socket-path $TESTNET_DIR/db/node.socket --state-dir $TESTNET_DIR/ledger-state --schema-dir $CARDANO_DB_SYNC_DIR/schema/ +RTS -p -hc -L200 -RTS" 'C-m'
 
 tmux -CC attach-session -t $session