The end of World War II saw an influx of new residents to Whidbey Island, putting a significant burden on the small phone company.

In 1953 local businessman David C. Henny purchased a controlling interest in Whidbey Telephone Company.

[1] Until 1961, Whidbey Telephone had overhead wires, and when the storms came, the lines went down due to wind, trees, and snow.

Whidbey Telephone became the first local phone company (west of the Rocky Mountains[3]) to provide Internet access to its customers in 1994.

For a few years, the company's Internet division, Whidbey.NET, even offered DSL to residents in Verizon territory on Whidbey Island and other local communities.

In 2016 Whidbey Telecom announced[6] it would be installing fiber optic cables to homes and businesses in its service area.

In 2019, Whidbey Telecom introduced The BiG GiG Fiber Network in Point Roberts, Washington.

At the same time, another company, Whidbey Connections, Inc. (WCI), was founded to serve customers of GTE on the north end of the island.

In 2005, the newly rebranded Whidbey Telecom Internet and Broadband began offering 5.5 Mbit/s DSL, and set their other speeds at 512 kbit/s, and 2.5 Mbit/s.

In the spring of 2009, Whidbey Telecom began upgrading customers, free of charge, from ADSL to ADSL2+ services.

Customers who signed up during the initial inquiries in 2015/2016, and whose accounts are in good standing will get the 1000 Mbit/s service for $70/mo, even if they are unable to be installed until 2025.

Most of this was owing to hardware costs, as integrated modem/router and ONT/routers were significantly more expensive than non-WiFi capable devices; but also to ensure modern security standards and performance were provided.

Additionally, support was very limited with the combination devices due to age and compatibility with newer consumer hardware.

Allowing the large number of fixed income residents to maintain their services with the peace of mind that they won't have a surprise bill due to a storm frying their lines, or children disconnecting critical items.

This shift was due to the dramatic rise in content costs and a fundamental change in the viewing habits of society from linear to streaming entertainment.

While it was a difficult decision by the company it enabled Whidbey Telecom to focus on strengthening its investment in its local fiber optic network to its customers.

Closed Circuit video services are also installed and used by businesses and residents alike, especially snowbirds, to ensure security of property, and provide evidence in cases of a holdup or robbery.

Whidbey Telecom's UL Listed Alarm Monitoring Center, is open 24/7 and located at their headquarters in Langley.