I am having a bit of a trouble correctly identifying sentences in a text for specific corner cases: If a dot, dot, dot is involved, this will not be kept. If " are involved. If a sentence accidentally start with a lower case. This is how I identify sentences in text so far (source: Subtitles Reformat to end with complete sentence): re.findall part basically looks for a chunk of str that starts with a capital letter, [A-Z], then anything except the punctuation, then ends with the punctuation, [\.?!]. import re text = "We were able to respond to the first research question. Next, we also determined the size of the population." for sentence in re.findall(r'([A-Z][^\.!?]*[\.!?])', text): print(sentence + "\n") We were able to respond to the first research question. Next, we also determined the size of the population. Corner Case 1: Dot, Dot, Dot The dot,dot,dot, is not kept, since there are no instructions given for what to do if three dots appear in a row. How could this be changed ? text = "We were able to respond to the first research question... Next, we also determined the size of the population." for sentence in re.findall(r'([A-Z][^\.!?]*[\.!?])', text): print(sentence + "\n") We were able to respond to the first research question. Next, we also determined the size of the population. Corner Case 2: " The "symbol is successfully kept within a sentence, but like the dot's following the punctuation, it will be deleted at the end. text = "We were able to respond to the first \"research\" question: \"What is this?\" Next, we also determined the size of the population." for sentence in re.findall(r'([A-Z][^\.!?]*[\.!?])', text): print(sentence + "\n") We were able to respond to the first "research" question: "What is this? Next, we also determined the size of the population. Corner Case 3: lower case start of a sentence If a sentence accidentally starts with a lower case, the sentence will be ignored. The aim would be to identify that a previous sentence ended (or the text just started) and hence a new sentence has to start. text = "We were able to respond to the first research question. next, we also determined the size of the population." for sentence in re.findall(r'([A-Z][^\.!?]*[\.!?])', text): print(sentence + "\n") We were able to respond to the first research question. Edit I tested it: import spacy from spacy.lang.en import English raw_text = 'Hello, world. Here are two sentences.' nlp = English() doc = nlp(raw_text) sentences = [sent.string.strip() for sent in doc.sents] ...but I get: --------------------------------------------------------------------------- ValueError Traceback (most recent call last) <ipython-input-157-4fd093d3402b> in <module>() 6 nlp = English() 7 doc = nlp(raw_text) ----> 8 sentences = [sent.string.strip() for sent in doc.sents] <ipython-input-157-4fd093d3402b> in <listcomp>(.0) 6 nlp = English() 7 doc = nlp(raw_text) ----> 8 sentences = [sent.string.strip() for sent in doc.sents] doc.pyx in sents() ValueError: [E030] Sentence boundaries unset. You can add the 'sentencizer' component to the pipeline with: nlp.add_pipe(nlp.create_pipe('sentencizer')) Alternatively, add the dependency parser, or set sentence boundaries by setting doc.is_sent_start. Continue reading...