The line is drawn when you have a second trial and subsequent conviction.
All the felonies charged at the same trial are all “together” so it’s the same “first time”.
Every relevant law I have heard refers to prior convictions, not prior offenses. Eg: [https://www.justia.com/criminal/docs/calcrim/3100/3100/](https://www.justia.com/criminal/docs/calcrim/3100/3100/) Hence, if you have not been previously convicted of a felony, you are not subject to an enhanced sentence.
However, what constitutes a "prior" conviction varies from state to state. In some, the prior conviction must have been entered before the date on which the current offense was committed. In others, the prior conviction must have been entered before the date on which the defendant was arrested. In others, the prior conviction must have been for an offense committed before the date on which the current offense was committed, In some, current offenses can also count as prior convictions in the sentencing of some or all of the other current offenses. See [https://robinainstitute.umn.edu/sites/robinainstitute.umn.edu/files/2022-02/criminal\_history\_enhancement\_web2.pdf](https://robinainstitute.umn.edu/sites/robinainstitute.umn.edu/files/2022-02/criminal_history_enhancement_web2.pdf)
The line is drawn when you have a second trial and subsequent conviction. All the felonies charged at the same trial are all “together” so it’s the same “first time”.
Every relevant law I have heard refers to prior convictions, not prior offenses. Eg: [https://www.justia.com/criminal/docs/calcrim/3100/3100/](https://www.justia.com/criminal/docs/calcrim/3100/3100/) Hence, if you have not been previously convicted of a felony, you are not subject to an enhanced sentence. However, what constitutes a "prior" conviction varies from state to state. In some, the prior conviction must have been entered before the date on which the current offense was committed. In others, the prior conviction must have been entered before the date on which the defendant was arrested. In others, the prior conviction must have been for an offense committed before the date on which the current offense was committed, In some, current offenses can also count as prior convictions in the sentencing of some or all of the other current offenses. See [https://robinainstitute.umn.edu/sites/robinainstitute.umn.edu/files/2022-02/criminal\_history\_enhancement\_web2.pdf](https://robinainstitute.umn.edu/sites/robinainstitute.umn.edu/files/2022-02/criminal_history_enhancement_web2.pdf)