diff --git a/Doc/library/plistlib.rst b/Doc/library/plistlib.rst
index 03cd3c1..7301d49 100644
--- a/Doc/library/plistlib.rst
+++ b/Doc/library/plistlib.rst
@@ -107,13 +107,6 @@
    An :exc:`OverflowError` will be raised for integer values that cannot
    be represented in (binary) plist files.
 
-   .. warning::
-
-      For compatibility with Apple's libraries it is possible to write
-      an integer in the range from 2 ** 63 upto (and including) 2 ** 64
-      to binary plists, even though these will be read back as negative
-      values.
-
    .. versionadded: 3.4
 
 
diff --git a/Lib/plistlib.py b/Lib/plistlib.py
index 8286456..dcb0f9c 100644
--- a/Lib/plistlib.py
+++ b/Lib/plistlib.py
@@ -879,18 +879,19 @@
                 try:
                     self._fp.write(struct.pack('>Bq', 0x13, value))
                 except struct.error:
-                    raise OverflowError(value)
+                    raise OverflowError(value) from None
             elif value < 1 << 8:
                 self._fp.write(struct.pack('>BB', 0x10, value))
             elif value < 1 << 16:
                 self._fp.write(struct.pack('>BH', 0x11, value))
             elif value < 1 << 32:
                 self._fp.write(struct.pack('>BL', 0x12, value))
+            elif value < 1 << 63:
+                self._fp.write(struct.pack('>BQ', 0x13, value))
+            elif value < 1 << 64:
+                self._fp.write(b'\x14' + value.to_bytes(16, 'big', signed=True))
             else:
-                try:
-                    self._fp.write(struct.pack('>BQ', 0x13, value))
-                except struct.error:
-                    raise OverflowError(value)
+                raise OverflowError(value)
 
         elif isinstance(value, float):
             self._fp.write(struct.pack('>Bd', 0x23, value))
diff --git a/Lib/test/test_plistlib.py b/Lib/test/test_plistlib.py
index a191608..bb7cc15 100644
--- a/Lib/test/test_plistlib.py
+++ b/Lib/test/test_plistlib.py
@@ -22,72 +22,73 @@
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-        VzVyUGdBQkFnTTgKCWJHOTBjeUJ2WmlCaWFXNWhjbmtnWjNWdWF6NEFBUUlE
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-        PC9kaWN0Pgo8L3BsaXN0Pgo='''),
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+        ZSBrZXkuPC9zdHJpbmc+CjwvZGljdD4KPC9wbGlzdD4K'''),
     plistlib.FMT_BINARY: binascii.a2b_base64(b'''
-        YnBsaXN0MDDfEA8BAgMEBQYHCAkKCwwNDg8QERImJy0uLzAxMjM1NDZXYUJp
-        Z0ludFVhRGF0ZVVhRGljdFZhRmxvYXRVYUxpc3RfEA9hTmVnYXRpdmVCaWdJ
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-        ARACVHRleHQjP+AAAAAAAAClKCkqIStRQVFCEAyjIyQsEAMT////7V+g4AAT
-        //////////tWRG9vZGFo0KARAtihNE8Q+jxsb3RzIG9mIGJpbmFyeSBndW5r
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-        AYsBlAGdAaQBpQGmAakBqwKoArYAAAAAAAACAQAAAAAAAAA3AAAAAAAAAAAA
-        AAAAAAAC0A=='''),
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+        AAAsM0GcuX30AAAA1RUWFxgZGhscHR5bYUZhbHNlVmFsdWVaYVRydWVWYWx1
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+        pSorLCMtUUFRQhAMoyUmLhADE////+1foOAAE//////////7VkRvb2RhaNCg
+        EQLYoTZPEPo8bG90cyBvZiBiaW5hcnkgZ3Vuaz4AAQIDPGxvdHMgb2YgYmlu
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+        az5fEBdUaGF0IHdhcyBhIHVuaWNvZGUga2V5LgAIACsAMwA8AEIASABPAFUA
+        ZwB0AHwAiACUAJoApQCuALsAygDTAOQA7QD4AQQBDwEdASsBNgE3ATgBTwFn
+        AW4BcAFyAXQBdgF/AYMBhQGHAYwBlQGbAZ0BnwGhAaUBpwGwAbkBwAHBAcIB
+        xQHHAsQC0gAAAAAAAAIBAAAAAAAAADkAAAAAAAAAAAAAAAAAAALs'''),
 }
 
 
@@ -106,6 +107,7 @@
             aFloat = 0.5,
             anInt = 728,
             aBigInt = 2 ** 63 - 44,
+            aBigInt2 = 2 ** 63 + 44,
             aNegativeInt = -5,
             aNegativeBigInt = -80000000000,
             aDict=dict(
@@ -152,7 +154,7 @@
 
     def test_int(self):
         for pl in [0, 2**8-1, 2**8, 2**16-1, 2**16, 2**32-1, 2**32,
-                   2**63-1, 1, -2**63]:
+                   2**63-1, 2**64-1, 1, -2**63]:
             for fmt in ALL_FORMATS:
                 with self.subTest(pl=pl, fmt=fmt):
                     data = plistlib.dumps(pl, fmt=fmt)
diff --git a/Mac/Tools/plistlib_generate_testdata.py b/Mac/Tools/plistlib_generate_testdata.py
index 68d4d74..057b617 100755
--- a/Mac/Tools/plistlib_generate_testdata.py
+++ b/Mac/Tools/plistlib_generate_testdata.py
@@ -1,6 +1,6 @@
 #!/usr/bin/env python3
 
-from Cocoa import NSMutableDictionary, NSMutableArray, NSString, NSDate
+from Cocoa import NSMutableDictionary, NSMutableArray, NSString, NSDate, NSNumber
 from Cocoa import NSPropertyListSerialization, NSPropertyListOpenStepFormat
 from Cocoa import NSPropertyListXMLFormat_v1_0, NSPropertyListBinaryFormat_v1_0
 from Cocoa import CFUUIDCreateFromString, NSNull, NSUUID, CFPropertyListCreateData
@@ -30,6 +30,7 @@
 
     seconds = datetime.datetime(2004, 10, 26, 10, 33, 33, tzinfo=datetime.timezone(datetime.timedelta(0))).timestamp()
     pl[nsstr('aBigInt')] = 2 ** 63 - 44
+    pl[nsstr('aBigInt2')] = NSNumber.numberWithUnsignedLongLong_(2 ** 63 + 44)
     pl[nsstr('aDate')] = NSDate.dateWithTimeIntervalSince1970_(seconds)
 
     pl[nsstr('aDict')] = d = OrderedDict()
diff --git a/Misc/NEWS b/Misc/NEWS
index 99214b7..5403a6a 100644
--- a/Misc/NEWS
+++ b/Misc/NEWS
@@ -109,6 +109,10 @@
 - Issue #15304: concurrent.futures.wait() can block forever even if
   Futures have completed. Patch by Glenn Langford.
 
+- Issue #14455: plistlib: fix serializing integers integers in the range
+  of an unsigned long long but outside of the range of signed long long for
+  binary plist files.
+
 IDLE
 ----