Exhibit 31.1

CERTIFICATION OF CHIEF EXECUTIVE OFFICER

I, Simon F. Nynens, President and Chief Executive Officer of Wayside Technology Group, Inc., certify that:

|1. | I have reviewed this annual report on Form 10-K of Wayside Technology Group, Inc;                                                                                                                                                                                                                                                    
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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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|3. | Based on my knowledge, the financial statements, and other financial information included in this  report, fairly present in all material respects the financial condition, results of operations and cash flows of the registrant as of, and for, the periods presented in this report;                                             
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|4. | The registrant's other certifying officers and I are responsible for establishing and maintaining disclosure controls and procedures (as defined in Exchange Act Rules 13a-15(e) and 15d-15(e)) and internal control over financial reporting (as defined in Exchange Act Rules 13a-15(f) and 15d-15(f)) for the registrant and have:
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|5. | The registrant's other certifying officers and I have disclosed, based on our most recent evaluation of internal control over financial reporting, to the registrant's auditors and the audit committee of the registrant's board of directors (or persons performing the equivalent functions):                                     
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|Date:  March 12, 2008                     | 
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|/s/ Simon F. Nynens                       | 
|Simon F. Nynens                           | 
|President and Chief Executive Officer and | 
|Chairman of the Board                     |