One solution to chronic teacher shortages has been to hire alternatively certified teachers who arrive in the classroom lacking critical trainings in methodology and pre-service student teaching. The problem addressed was the high rate of attrition for alternatively trained teachers in public and private schools who leave the profession within the first few years as compared to those trained traditionally. The purpose was to identify the specific challenges teachers in their first years in Catholic secondary schools face and the types of professional development available. High attrition rates disrupt schools and negatively impact student learning. The conceptual framework was built on five key concepts: hierarchies of knowledge, preservice training, inductions, attrition, and retention. Utilizing a qualitative, transcendental phenomenological design, non-criterion sampling was used to identified participants, nine of whom agreed to one 45–60-minute interview. Transcripts were subjected to two-cycle coding from which a set of themes emerged. Themes for the first question, how beginning alternatively prepared teachers in secondary Catholic schools describe their instructional and management challenges in the classroom, were the following: lacking knowledge and understanding, baptism by fire, and learning through resourcefulness. Themes for the second question, types of professional development made available to alternatively trained teachers, were the following: targeted archdiocesan trainings support acquisition of instructional techniques, on-site supervisor supports acquisition of instructional techniques, and informal supports from peers help participants acquire instructional techniques. Results from the two questions revealed alternatively trained teachers make decisions informed by assumptions and confusion resulting in short- and long-term consequences; improved management depends upon the ability to modify personality; resourcefulness supplements consistent supports; professional development targeting practical instructional strategies improves classroom practice; administrators play a pivotal role; and informal networks support colleagues. Recommendations include the need for intensive trainings prior to entering the classroom, support for technology management and use, and greater supports from administrators and colleagues. Future studies should expand the scope of the research to archdioceses in other regions, expand the sample size, and investigate whether targeted instructional supports linked to student achievement improve supports for alternatively trained teachers.