Abstract 1‐Azaspirocycles are important structures present in many drugs and natural products. This work describes the silver‐catalyzed tandem cyclization strategy, which provides atom‐economical access to various azaoxa‐ and diazaspirocycles from alkynes containing two appended oxygen‐ and nitrogen‐based nucleophiles. Intramolecular attack of the pendant nucleophile on the in situ‐generated iminium intermediate is the key to the success of this transformation.