As described in https://www.python.org/dev/peps/pep-0327/#rounding-algorithms
round-half-up: If the discarded digits represent greater than or equal to half (0.5) then the result should be incremented by 1; otherwise the discarded digits are ignored.

Rounding 9.95 to 1 decimal with ROUND_HALD_UP results in 9.9 instead of 10.0:
 
Decimal(9.95).quantize(Decimal('1.1'),ROUND_HALF_UP)
Out[49]: Decimal('9.9')

It does not matter at wich position this rounding with influence on another digit happens:

Decimal(9.995).quantize(Decimal('1.11'),ROUND_HALF_UP)
Out[50]: Decimal('9.99')

It is a specific problem with the 5, because 9.96 works as expected

Decimal(9.96).quantize(Decimal('1.1'),ROUND_HALF_UP)
Out[40]: Decimal('10.0')

System:

Python 3.6.4

import decimal
decimal.__version__ : '1.70'

This isn't a bug. When you do `Decimal(9.95)`, you're converting the binary floating-point number `9.95` to a `Decimal` instance. The conversion is performed exactly, with no change in the value. But the *input* to the conversion, the float `9.95` can't be stored exactly in IEEE 754 binary64 format, so what you end up with is something very slightly smaller.

>>> from decimal import Decimal
>>> Decimal(9.95)
Decimal('9.949999999999999289457264239899814128875732421875')

That's the reason that it rounds down.

Good practice is to create your Decimal instances from strings rather than floats.

>>> Decimal(9.95).quantize(Decimal('1.1'),ROUND_HALF_UP)
Decimal('9.9')
>>> Decimal('9.95').quantize(Decimal('1.1'),ROUND_HALF_UP)
Decimal('10.0')