As the NFL offseason approaches, the San Francisco 49ers are quietly facing one of the most consequential roster junctures of their recent competitive window, with sweeping personnel decisions looming as the new league year draws closer.

When the NFL calendar officially flips on March 11, San Francisco will see a total of 28 players from its current roster reach some form of free agency, creating significant uncertainty across multiple position groups.

Of those 28 players, 21 are set to become unrestricted free agents, six are classified as restricted free agents, and one falls under the exclusive rights free agent designation, reflecting the breadth of roster turnover facing the organization.

The lone exclusive rights free agent is offensive lineman Austen Pleasants, whose contractual situation heavily favors the team due to the restrictive nature of ERFA rules within the NFL’s collective bargaining framework.

Unless the 49ers elect not to tender Pleasants an offer, which remains highly unlikely, he is expected to return for the offseason program and remain part of San Francisco’s offensive line depth moving forward.

While Pleasants appears to be a straightforward retention, the remaining 27 players present a far more complex evaluation process involving salary cap implications, positional value, durability, and schematic fit within Kyle Shanahan’s system.

It is unrealistic to expect the 49ers to retain every departing free agent, especially given their long-term financial commitments to core stars across both sides of the ball.

However, several of those pending free agents stand out as logical retention candidates, either due to on-field production, locker room presence, or their ability to stabilize key units during a period of transition.

Among the most discussed names is wide receiver Jauan Jennings, whose future with the organization once appeared uncertain during a turbulent offseason.

Earlier indications suggested a possible split between Jennings and the team, particularly after contract-related tensions surfaced during training camp and raised questions about his long-term role.

Despite that backdrop, Jennings once again emerged as a reliable contributor, leading the 49ers’ wide receiver group in production for the second consecutive season.

Although his overall numbers dipped slightly during the 2025 campaign, Jennings still recorded 643 receiving yards and posted a career-high nine touchdowns on 55 receptions.

Those numbers become more impressive when viewed in context, as Jennings battled a series of nagging injuries throughout the season that limited his practice availability and in-game explosiveness.

Turning 29 years old in July, Jennings now enters unrestricted free agency for the first time, a milestone that typically encourages players to explore the open market aggressively.

Still, the combination of age, injury history, and positional market dynamics could temper external interest, potentially allowing San Francisco to negotiate a team-friendly extension.

For the 49ers, retaining Jennings would provide much-needed continuity within a receiving corps that has struggled with availability and consistency over multiple seasons.

A modest multi-year deal could keep Jennings in the Bay Area into his early 30s while preserving offensive chemistry in a system heavily reliant on timing and trust.

If Jennings represents stability on offense, kicker Eddy Pineiro may be the single most dependable performer on the entire roster entering free agency.

Pineiro’s 2025 season bordered on historic, as he converted 96.6 percent of his field goal attempts, the highest success rate among all NFL kickers.

His lone miss came on a 64-yard attempt in Indianapolis, a kick that struck the crossbar and would have been considered ambitious under nearly any circumstances.

Excluding that attempt, Pineiro finished a flawless 28-for-28 on field goals, a level of consistency that is exceedingly rare in today’s league.

Even more critical, he delivered under postseason pressure, going three-for-three across two road playoff games, reinforcing his reliability in high-leverage moments.

For a franchise that endured instability at kicker following uneven seasons from Jake Moody, Pineiro provided something invaluable: certainty.

Given the narrow margins that define playoff success, retaining Pineiro should rank among the organization’s highest offseason priorities.

Along the defensive front, restricted free agent Kalia Davis quietly established himself as a dependable rotational contributor during the 2025 season.

Davis appeared in all 17 regular-season games, surpassing his combined total from his first two NFL seasons and demonstrating improved durability and consistency.

Originally selected in the sixth round, Davis required time to adjust to the physical demands of the professional game, but his development trajectory is now trending upward.

San Francisco’s defensive line depth was tested repeatedly throughout the season, and Davis emerged as a reliable option within the interior rotation.

While the team is not obligated to tender him at a high level, a multi-year extension could secure valuable depth at a modest cost.

Another restricted free agent drawing attention is tight end Jake Tonges, whose role expanded significantly following George Kittle’s Achilles injury.

Tonges exceeded expectations as a pass-catching option, finishing the season with 34 receptions, 293 yards, and five touchdowns.

His production offered a glimpse into his potential as both a short-term replacement and long-term complement within San Francisco’s tight end room.

With Kittle’s recovery timeline uncertain, maintaining continuity at the position becomes a strategic necessity rather than a luxury.

Whether through a tender or a multi-year contract, keeping Tonges in the building aligns with both immediate needs and future roster planning.

On the offensive line, Spencer Burford presents a classic depth-versus-upside evaluation for the front office.

Burford eventually settled in as the starting left guard after Ben Bartch suffered an injury, providing stability during a turbulent stretch.

His positional versatility allows him to play four different spots along the offensive line, a trait that carries significant value in Shanahan’s scheme.

While he may not represent the long-term answer at left guard, Burford profiles as a capable swing lineman who can absorb injuries without derailing the offense.

Retaining him at the right price would preserve flexibility without limiting the team’s ability to pursue upgrades.

Special teams contributions also factor into offseason decisions, and wide receiver Skyy Moore fits squarely into that category.

Moore’s offensive involvement remained minimal, but his impact as a kickoff returner altered field position in several key games.

By season’s end, opposing teams deliberately kicked away from him, a clear sign of respect for his return ability.

While not essential, Moore’s special teams value alone may justify another short-term contract.

Finally, defensive lineman Jordan Elliott represents one of the most nuanced decisions of the offseason.

At 28 years old, Elliott remains effective but could command a salary above what teams typically allocate to rotational interior linemen.

However, pairing Elliott with Davis while integrating younger talents like CJ West and Alfred Collins would provide a balanced defensive tackle group.

If Elliott’s market remains reasonable, retaining his experience and reliability could stabilize a unit that struggled with depth throughout the season.

Ultimately, the 49ers’ offseason will be defined not by splash signings, but by calculated retention decisions that preserve their championship window.

Each contract choice will reflect a delicate balance between present competitiveness and long-term sustainability.

How San Francisco navigates these 28 impending free agents may determine whether their next season ends in contention—or transition.