Why doesn't str.replace replace ALL values in selected pandas dataframe column?

You were on the right track. Replace raw string as follows

summary['Labels'] = summary['Labels'].str.replace(r'test\|','', regex=True)



Labels
0  test 1
1  test 2
2  test 4

Try str.extract:

df['Labels'] = df['Labels'].str.extract(r'\|(.*)', expand=False) \
                           .combine_first(df['Labels'])
print(df)

# Output
   Labels
0  test 1
1  test 2
2  test 3
3  test 4
4  test 5
5  test 6