Pathogenic bacteria demonstrate incredible abilities to evade conventional antibiotics through the development of resistance and formation of dormant, surface-attached biofilms. Therefore, agents that target and eradicate planktonic and biofilm bacteria are of significant interest. We explored a new series of halogenated phenazines (HP) through the use of <i>N</i>-aryl-2-nitrosoaniline synthetic intermediates that enabled functionalization of the 3-position of this scaffold. Several HPs demonstrated potent antibacterial and biofilm-killing activities (<i>e.g.</i>, HP <b>29</b>, against methicillin-resistant <i>Staphylococcus aureus</i>: MIC = 0.075 μM; MBEC = 2.35 μM), and transcriptional analysis revealed that HPs <b>3</b>, <b>28</b>, and <b>29</b> induce rapid iron starvation in MRSA biofilms. Several HPs demonstrated excellent activities against <i>Mycobacterium tuberculosis</i> (HP <b>34</b>, MIC = 0.80 μM against CDC1551). This work established new SAR insights, and HP <b>29</b> demonstrated efficacy in dorsal wound infection models in mice. Encouraged by these findings, we believe that HPs could lead to significant advances in the treatment of challenging infections.