According to the Centers for Disease Control and Prevention statistics, about 6.2 million adults in the United States have heart failure. Guideline-Directed Medical Therapy (GDMT) involving the use of renin-angiotensin-aldosterone system inhibitors with or without a neprilysin inhibitor, β-blockers, mineralocorticoid-receptor-antagonists, and sodium-glucose cotransporter-2 inhibitors serve as the backbone for heart failure with reduced ejection fraction (HFrEF) therapy. However, in patients with refractory hypotension, the initiation of GDMT may not be possible. We present four cases where the use of midodrine, an alpha adrenergic agonist, serves as bridge therapy for the initiation or continuation of GDMT with marked clinical improvement. These cases illustrate how exacerbations of HFrEF may be ameliorated with outpatient midodrine titration among patients with baseline, persistent hypotension such that GDMT may be better tolerated.