The development of technology, data-driven systems and applications are constantly revolutionizing our lives. We are surrounded by digitized systems/solutions that are transforming and making our lives easier. The criticality and complexity behind these systems are immense. So as to meet user satisfaction and keep up with the business needs, these digital systems should possess high availability, minimum downtime, and mitigate cyber attacks. Hence, system monitoring becomes an integral part of the lifecycle of a digital product/system. System monitoring often includes monitoring and analyzing logs outputted by the systems containing information about the events occurring within a system. The first step in log analysis generally includes understanding and segregating the various logical components within a log line, termed log parsing. Traditional log parsers use regular expressions and human-defined grammar to extract information from logs. Human experts are required to create, maintain and update the database containing these regular expressions and rules. They should keep up with the pace at which new products, applications and systems are being developed and deployed, as each unique application/system would have its own set of logs and logging standards. Logs from new sources tend to break the existing systems as none of the expressions match the signature of the incoming logs. The reasons mentioned above make the traditional log parsers time-consuming, hard to maintain, prone to errors, and not a scalable approach. On the other hand, machine learning based methodologies can help us develop solutions that automate the log parsing process without much intervention from human experts. NERLogParser is one such solution that uses a Bidirectional Long Short Term Memory (BiLSTM) architecture to frame the log parsing problem as a Named Entity Recognition (NER) problem. There have been recent advancements in the Natural Language Processing (NLP) domain with the introduction of architectures like Transformer and Bidirectional Encoder Representations from Transformers (BERT). However, these techniques have not been applied to tackle the problem of information extraction from log files. This gives us a clear research gap to experiment with the recent advanced deep learning architectures. This thesis extensively compares different machine learning based log parsing approaches that frame the log parsing problem as a NER problem. We compare 14 different approaches, including three traditional word-based methods: Naive Bayes, Perceptron and Stochastic Gradient Descent; a graphical model: Conditional Random Fields (CRF); a pre-trained sequence-to-sequence model for log parsing: NERLogParser; an attention-based sequence-to-sequence model: Transformer Neural Network; three different neural language models: BERT, RoBERTa and DistilBERT; two traditional ensembles and three different cascading classifiers formed using the individual classifiers mentioned above. We evaluate the NER approaches using an evaluation framework that offers four different evaluation schemes that not just help in comparing the NER approaches but also help us assess the quality of extracted information. The primary goal of this research is to evaluate the NER approaches on logs from new and unseen sources. To the best of our knowledge, no study in the literature evaluates the NER methodologies in such a context. Evaluating NER approaches on unseen logs helps us understand the robustness and the generalization capabilities of various methodologies. To carry out the experimentation, we use In-Scope and Out-of-Scope datasets. Both the datasets originate from entirely different sources and are entirely mutually exclusive. The In-Scope dataset is used for training, validation and testing purposes, whereas the Out-of-Scope dataset is purely used to evaluate the robustness and generalization capability of NER approaches. To better deal with logs from unknown sources, we propose Log Diversification Unit (LoDU), a unit of our system that enables us to carry out log augmentation and enrichment, which helps make the NER approaches more robust towards new and unseen logs. We segregate our final results on a use-case basis where different NER approaches may be suitable for various applications. Overall, traditional ensembles perform the best in parsing the Out-of-Scope log files, but they may not be the best option to consider for real-time applications. On the other hand, if we want to balance the trade-off between performance and throughput, cascading classifiers can be considered the go-to solution.