Soil amendments with varying carbon:nitrogen (C:N) ratios [grass clippings, wheat (Triticum aestivum), straw, sawdust] were pre-plant incorporated into 12 × 15-ft field plots at ≈4 tons/acre in fall and then planted to perennial strawberry (Fragaria ×ananassa) the following spring and grown 4 years. These amendments were intended to alter soil biological activity as measured by a suite of soil tests referred to as “soil health indicators” which, in turn, were hypothesized to affect strawberry plant growth and yield. In addition, plots were either tilled deeply or shallowly to determine if intensity of tillage affected soil health indicators. After the first and second years, amendments were reapplied between rows and soil and plant variables continued to be monitored. Soil respiration was consistently higher in plots with higher C:N amendments, with up to a 189% increase in respiration in sawdust-amended plots over unamended plots. The respiration rate was highest in sawdust-amended shallow-tilled plots; however, in most cases, tillage depth had no effect on other soil or plant variables. Potentially mineralizable N was higher in sawdust-amended plots in May both years, but not throughout the rest of the season. Soil moisture and pH were 21% and 2% higher, respectively, between the rows of strawberries than within the rows by September of the planting year, and remained that way throughout the next year. Neither the C:N ratio of the soil nor the foliar nutrient concentration of strawberry leaves was affected by the C:N ratio of the amendments. Most significantly, plant density and yield were depressed up to 42% and 26%, respectively, by planting into straw-amended soil, but planting into other amendments did not have this effect. After the second fruiting year (the third growing season), only straw was incorporated into half of the plots after harvest to mimic winter straw mulch incorporation, and yield was measured again the following spring. However, incorporation of straw between rows after plants were established did not affect yield. This study corroborates the general recommendation to avoid new strawberry plantings in locations that were recently planted to strawberry, as old fields likely harbor pathogens and contain undecomposed straw residue from previous years’ mulching that could depress yield. Despite differences in soil health indicators between amendment and tillage treatments, yield differences were not correlated with them. These observations suggest that alternative soil health indicators may be better suited for perennial strawberry.