Exhibit 31.1

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CERTIFICATION OF CHIEF EXECUTIVE OFFICER

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I, Dale Foster, certify that:

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1.I have reviewed this annual report on Form 10-K/A of Wayside Technology Group, Inc; and

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2.

Based on my knowledge, this report does not contain any untrue statement of a material fact or omit to state a material fact necessary to make the statements made, in light of the circumstances under which such statements were made, not misleading with respect to the period covered by this report.

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Date: April 29, 2020

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/s/ Dale Foster

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Dale Foster

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Chief Executive Officer and Director

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