diff --git a/test/functional/test_framework/messages.py b/test/functional/test_framework/messages.py
--- a/test/functional/test_framework/messages.py
+++ b/test/functional/test_framework/messages.py
@@ -500,9 +500,15 @@
         return self.sha256
 
     def __repr__(self):
+        # time.ctime suffers from the 2038 Problem on some modern OSs, so limit
+        # what timestamps are pretty-printed until this is fixed.
+        displayTime = self.nTime
+        if abs(displayTime) <= pow(2, 31):
+            displayTime = time.ctime(displayTime)
+
         return "CBlockHeader(nVersion={} hashPrevBlock={:064x} hashMerkleRoot={:064x} nTime={} nBits={:08x} nNonce={:08x})".format(
             self.nVersion, self.hashPrevBlock, self.hashMerkleRoot,
-            time.ctime(self.nTime), self.nBits, self.nNonce)
+            displayTime, self.nBits, self.nNonce)
 
 
 class CBlock(CBlockHeader):
@@ -559,9 +565,15 @@
             self.rehash()
 
     def __repr__(self):
+        # time.ctime suffers from the 2038 Problem on some modern OSs, so limit
+        # what timestamps are pretty-printed until this is fixed.
+        displayTime = self.nTime
+        if abs(displayTime) <= pow(2, 31):
+            displayTime = time.ctime(displayTime)
+
         return "CBlock(nVersion={} hashPrevBlock={:064x} hashMerkleRoot={:064x} nTime={} nBits={:08x} nNonce={:08x} vtx={})".format(
             self.nVersion, self.hashPrevBlock, self.hashMerkleRoot,
-            time.ctime(self.nTime), self.nBits, self.nNonce, repr(self.vtx))
+            displayTime, self.nBits, self.nNonce, repr(self.vtx))
 
 
 class PrefilledTransaction:
@@ -969,8 +981,14 @@
         return r
 
     def __repr__(self):
+        # time.ctime suffers from the 2038 Problem on some modern OSs, so limit
+        # what timestamps are pretty-printed until this is fixed.
+        displayTime = self.nTime
+        if abs(displayTime) <= pow(2, 31):
+            displayTime = time.ctime(displayTime)
+
         return 'msg_version(nVersion={} nServices={} nTime={} addrTo={} addrFrom={} nNonce=0x{:016X} strSubVer={} nStartingHeight={} nRelay={})'.format(
-            self.nVersion, self.nServices, time.ctime(self.nTime),
+            self.nVersion, self.nServices, displayTime,
             repr(self.addrTo), repr(self.addrFrom), self.nNonce,
             self.strSubVer, self.nStartingHeight, self.nRelay)