1996: Thinking that Rosanna had moved on with Scott, a dejected Mike slept with Carly again and got her pregnant. Rosanna, who had by then rekindled her relationship with Mike, stunned everyone by agreeing to accept his child. She offered Carly $10 million to let her raise the baby with Mike, who was disgusted to hear of the plan. There were more breakups and makeups — as well as another aborted wedding — between the star-crossed lovers, but the romance finally died after Carly miscarried the baby following a confrontation with Rosanna, who left town shortly thereafter. But first, she set up a $50 million trust fund for Carly's next baby — provided Mike wasn't the father.

1999: Having amended the trust fund to give Carly a deadline (and the caveat that she had to be married to the father), a hardened Rosanna returned to meet her new nephew, Parker, and check up on her sister. She stuck around long enough to flirt with Carly's then-husband, Brad, and cancel the trust fund after Brad vengefully revealed that Parker's paternity test had been switched.

2002: Rosanna came back to Oakdale again, horrified to learn that Carly — who she blamed for ruining her life — had evolved into a fairly upstanding, beloved citizen. She shamelessly flirted with Mike, but fell for Craig, who was still in love with Carly (which only made Ro more determined to win him). She also befriended her sister's chief rival, Barbara, and provided financial backing for BRO, while clashing with Craig's daughter, Lucy. The teen spotted Rosanna impulsively kissing Mike, but Ro caught her spending time with forbidden beau Aaron. They made a deal to keep the secrets from Craig, but an annoyed Lucy reneged and spilled all to daddy. After Babs also tattled to Craig that Rosanna was just playing him, he dumped her. She eventually got Craig back and gave him full control of BRO, while also butting heads with Lucy and Aaron. When Craig wanted to hire Carly as a designer, Rosanna initiated the "Carly Clause": If he got romantic with her sister, he'd lose BRO, which he had renamed Monte Carlo. She then plotted to ruin both Mike's relationship with Molly and Carly's wedding to Jack, while having her husband and sister followed by Henry. He managed to observe something very incriminating: Carly slept with another man before her wedding to Jack. Assuming the other man was Craig, Rosanna threatened to spill all unless Carly left Jack and Monte Carlo. She later suspected that Mike was the other man, after Carly took $50,000 from Monte Carlo to silence Henry. In the midst of all this, Rosanna's doctor told her that she needed a hysterectomy. She admitted the truth to her sympathetic sister in a weak moment.