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Issue #<3921> may be the same problem.
Sending Gmail by smtplib fails on Python 3.0 and 3.0.1.
It seems to be exist two problems in encode_plain function in smtplib.py:
 * parameter of encode_base64 must be bytes, not str,
 * by default, encode_base64 adds extra newline.
The following is an example of patch.
# original version
def encode_plain(user, password):
 return encode_base64("0円%s0円%s" % (user, password))
# fixed version. Note that "eol=''" is given in Python 2.6's smtplib.
def encode_plain(user, password):
 s = "0円%s0円%s" % (user, password)
 return encode_base64(s.encode('ascii'), eol='')

Can you show us the failing application? Most likely, the bug is in your
code, not in Python.

The attached test script works fine in Python 2.6.
Replace the following texts in the script:
from@gmail.com
to@gmail.com
password

The attachment is output of smtptest.py on Python 3.0.

sorry, pressed the wrong button.
that solution does work. didn't find this until #python helped me get:
return encode_base64( ("0円%s0円%s" % (user, password) ).encode('ascii') )

I add simple smtp auth unit test to exercise this bug.

Martin: see a test script in issue 3921.

5304 and 3921 are fixed. Is there still an issue here? If so, I think
we need a test case we can add to the test suite. It can be a patch
against the new test_smtpnet.py test.

Looks like I accidentally deleted the file I was asking for. Not sure
how that happened, but I'm reattaching it.

There is a similar problem that I found with encode_cram_md5 in 
smtplib.py, SMTP.login() method. I used the solution proposed by miwa, 
both for PLAIN and CRAM MD5 authentication. Additionally, for the last 
one, I had to introduce a second correction and byte encode the 
password string when passing it to hmac.HMAC. 
I do not know if I did things correctly, but just in case it can help 
here is the complete patch that I used and worked well with the two 
AUTH methods. I keep the original and modified lines for clarity.
def encode_cram_md5(challenge, user, password):
 challenge = base64.decodestring(challenge)
 #response = user + " " + hmac.HMAC(password, 
challenge).hexdigest()
 response = user + " " + hmac.HMAC(password.encode(), 
challenge).hexdigest()
 #return encode_base64(response)
 return encode_base64((response).encode('ascii'), eol='')
 
 def encode_plain(user, password):
 #return encode_base64("0円%s0円%s" % (user, password))
 return encode_base64(("0円%s0円%s" % (user, password)).encode
('ascii'), eol='')

Committed the simple auth tests and fix in r72868 in py3k and r72877 in
3.0. Also added the test to trunk in r72878 to keep the test source in
sync, and to 26maint similarly in r72886.
Now we need tests for the other auth cases.

LOGIN and CRAM-MD5 login are fixed in r72990 (3.1) and r72991 (3.0).