FOURTEENTH LOAN MODIFICATION AGREEMENT

Exhibit 10.22(o)

FOURTEENTH LOAN MODIFICATION AGREEMENT

This Fourteenth Loan Modification Agreement (this “Loan Modification Agreement”) is entered into on June 28, 2007 by and between SILICON VALLEY BANK, a California chartered bank, with its principal place of business at 0000 Xxxxxx Xxxxx, Xxxxx Xxxxx, Xxxxxxxxxx 00000 and with a loan production office located at One Xxxxxx Executive Park, Suite 200, 0000 Xxxxxxxxxx Xxxxxx, Xxxxxx, Xxxxxxxxxxxxx 00000 (“Bank”) and ASPEN TECHNOLOGY, INC., a Delaware corporation with offices at Xxx Xxxxx Xxxx, Xxxxxxxxx, Xxxxxxxxxxxxx 00000 for itself and as successor by merger with ASPENTECH, INC., a Texas corporation with offices at Xxx Xxxxx Xxxx, Xxxxxxxxx, Xxxxxxxxxxxxx 00000 (“Borrower”).

1. DESCRIPTION OF EXISTING INDEBTEDNESS AND OBLIGATIONS. Among other indebtedness and obligations which may be owing by Borrower to Bank, Borrower is indebted to Bank pursuant to a loan arrangement dated as of January 30, 2003, evidenced by, among other documents, a certain Loan and Security Agreement dated as of January 30, 2003 between Borrower, Aspentech, Inc. and Bank, as amended by a certain letter agreement dated February 14, 2003, a certain First Loan Modification Agreement dated June 27, 2003, a certain Second Loan Modification Agreement dated September 10, 2004, a certain Third Loan Modification Agreement dated January 28, 2005, a certain Fourth Loan Modification Agreement dated April 1, 2005, a certain Fifth Loan Modification Agreement dated May 6, 2005, a certain Sixth Loan Modification Agreement dated June 15, 2005, a certain Seventh Loan Modification Agreement dated September, 2005, a certain Eighth Amendment to Loan and Security Agreement dated November 22, 2005, a certain Ninth Loan Modification Agreement dated July 17, 2006, a certain Tenth Loan Modification Agreement dated September 15, 2006, a certain Eleventh Loan Modification Agreement dated September 27, 2006, a certain Twelfth Loan Modification Agreement dated January 12, 2007 and a certain Thirteenth Loan Modification Agreement dated April 13, 2007 (as amended, the “Loan Agreement”). Capitalized terms used but not otherwise defined herein shall have the same meaning as in the Loan Agreement,

2. DESCRIPTION OF COLLATERAL. Repayment of the Obligations is secured by the Collateral as described in the Loan Agreement (together with any other collateral security granted to Bank, the “Security Documents”).

Hereinafter, the Security Documents, together with all other documents evidencing or securing the Obligations shall be referred to as the “Existing Loan Documents.”

3. DESCRIPTION OF CHANGE IN TERMS.

Modifications to Loan Agreement.

(i) The Loan Agreement shall be amended by deleting the following text appearing in the definition of “Eligible Receivables” in Section 8 of the Loan Agreement:

“(viii) the Receivable must not be owing from an Account Debtor located outside of the United States or Canada that is deemed unacceptable by Silicon in its discretion;”

and inserting in lieu thereof the following:

“(viii) the Receivable must not be owing from an Account Debtor located outside of the United States or Canada that is deemed unacceptable by Silicon in its discretion; provided, further, that such Receivables shall in no event be deemed to be acceptable to Silicon to the extent the aggregate amount of advances and other financial accommodations based upon such Receivables exceeds $10,000,000 unless specifically approved by Silicon in writing in each instance;”

(ii) The Loan Agreement shall be amended by deleting the following text appearing in Section 1 of the Schedule to the Loan Agreement:

(i) $25,000,000 (the “Maximum Credit Limit;” minus

and inserting in lieu thereof the following:

(i) $25,000,000 (or such lesser amount necessary to ensure that the aggregate amount of the Obligations under this Agreement plus the aggregate amount of Purchased Receivables (as defined in the Non-Recourse Receivables Purchase Agreement between Silicon and Borrower dated December 31, 2003, as amended and as may be further amended and in effect from time to time) do not exceed $80,000,000) (the “Maximum Credit Limit”); minus

(iii) The Loan Agreement shall be amended by deleting the following text appearing in Section 4 of the Schedule to the Loan Agreement:

“MATURITY DATE

(Section 6.1): July 16, 2007”

and inserting in lieu thereof the following:

“MATURITY DATE

(Section 6.1): October 16, 2007”

(iv) The Loan Agreement shall be amended by deleting Section 5(a) of the Schedule thereto in its entirety and inserting in lieu thereof the following:

“a. Minimum Tangible Net Worth:

Borrower shall at all times maintain, to be tested monthly, as of the last day of each month, a Tangible Net Worth of not less than the sum of (i) plus (ii) below:

(i)

(a) from April 1, 2005 through and including April 30, 2005 - $35,000,000;

(b) from May 1, 2005 through and including May 31, 2005 - $25,000,000;

(d) from July 1, 2005 through and including July 31, 2005 - $14,000,000;

(e) from August 1, 2005 through and including August 31, 2005 - $7,000,000;

(f) from September 1, 2005 through and including September 30, 2005 - $21,000,000;

(g) from October 1, 2005 through and including October 31, 2005 - $14,000,000;

(h) from November 1, 2005 through and including November 30, 2005 - $7,000,000;

(i) from December 1, 2005 through and including December 31, 2005 - $26,000,000;

(j) from January 1, 2006 through and including January 31, 2006 - $19,000,000;

(k) from February 1, 2006 through and including February 28, 2006-$l2,000,000;

(l) from March 1, 2006 through and including March 31, 2006 - $31,000,000;

(m) from April 1, 2006 through and including April 30, 2006 -$24,000,000;

(n) from May 1, 2006 through and including May 31, 2006 - $17,000,000;

(o) from June 1, 2006 through and including June 30, 2006 - $36,000,000;

(p) from July 1, 2006 through and including July 31, 2006 - $29,000,000;

(q) from August 1, 2006 through and including August 31, 2006 - $22,000,000;

(r) from September 1, 2006 through and including September 30, 2006 - $41,000,000;

(s) from October 1, 2006 through and including October 31, 2006 - $34,000,000;

(t) from November 1, 2006 through and including November 30, 2006 - $27,000,000;

(u) from December 1, 2006 through and including December 31, 2006 - $40,000,000;

(v) from January 1, 2007 through and including January 31, 2007 - $32,000,000;

(w) from February 1, 2007 through and including February 28, 2007 - $24,000,000;

(x) from March 1, 2007 through and including March 31, 2007 - $40,000,000;

(z) from April 1, 2007 through and including April 30, 2007 - $32,000,000;

(aa) from May 1, 2007 through and including May 31, 2007 - $24,000,000;

(bb) from June 1, 2007 through and including June 30, 2007 - $60,000,000;

(cc) from July 1, 2007 through and including July 31, 2007 - $52,000,000;

(dd) from August 1, 2007 through and including August 31, 2007 - $54,000,000;

(ee) from September 1, 2007 and thereafter - $60,000,000;

(ii) 75% of all consideration received after July 1, 2005 from proceeds from the issuance of any equity securities of the Borrower (other than (i)

the issuance of stock options, restricted stock or other stock-based awards under the Borrower’s director or employee stock incentive plans, or (ii) stock purchases under the Borrower’s employee stock purchase plan).”

(v) The loan Agreement shall be amended by deleting Section 5(c) of the Schedule thereto in its entirety and inserting in lieu thereof the following:

“c. Adjusted Quick Ratio:

Borrower shall maintain, at all times, to be tested monthly, an Adjusted Quick Ratio of at least:

(a) from April 1, 2005 through and including April 30, 2005 - 1.35 to 1.0;

(b) from May 1, 2005 through and including May 31, 2005 - 1.20 to 1.0;

(d) from July 1, 2005 through and including July 31, 2005 - 1.05 to 1.0;

(e) from August 1, 2005 through and including August 31, 2005 - 0.95 to 1.0;

(f) from September 1, 2005 through and including September 30, 2005 - 1.1.5 to 1.0;

(g) from October 1, 2005 through and including October 31, 2005 - 1.05 to 1.0;

(h) from November 1, 2005 through and including November 30, 2005 - 0.95 to 1.0;

(i) from December 1, 2005 through and including December 31, 2005 — 1.20 to 1.0

(j) from January 1, 2006 through and including January 31, 2006 - 1.10 to 1.0;

(k) from February 1, 2006 through and including February 28, 2006 - 1.00 to 1.0;

(1) from March 1, 2006 through and including March 31, 2006 - 1.25 to 1.0;

(m) from April 1, 2006 through and including April 30, 2006 - 1.15 to 1.0;

(n) from May 1, 2006 through and including May 31, 2006 — 1.05 to 1.0;

(o) from June 1, 2006 through December 31, 2006 - 1.25 to 1.0;

(p) from January 1, 2007 through and including February 28, 2007 -1.15 to 1.0;

(q) from March 1, 2007 through and including March 31, 2007 - 1.25 to 1.0;

(r) from April 1, 2007 through and including May 31, 2007 - 1.15 to 1.0; and

(s) from June 1, 2007 and thereafter - 1.50 to 1.0.”

4. FEES. Borrower shall pay to Bank a modification fee of $22,500.00, which fee shall be due on the date hereof and shall be deemed fully earned as of the date hereof. Borrower shall also reimburse Bank for all legal fees and expenses incurred in connection with this amendment to the Existing Loan Documents.

5. RATIFICATION OF NEGATIVE PLEDGE. Borrower hereby ratifies, confirms and reaffirms, all and singular, the terms and conditions of a certain Negative Pledge Agreements each dated as of January 30, 2003 between Borrower and Bank, and acknowledges, confirms and agrees that said Negative Pledge Agreement shall remain in full force and effect.

6. RATIFICATION OF PERFECTION CERTIFICATES. Borrower hereby ratifies, confirms and reaffirms, all and singular, the terms and disclosures contained in certain Perfection Certificates each dated as of January 30, 2003, as amended and affected by Schedule 1 to the Fourth Amendment and Exhibit A to the Fourth Amendment and acknowledges, confirms and agrees the disclosures and information therein, in Schedule 3.10 to the Loan Agreement, in on Schedule 1 annexed to the Tenth Loan Modification Agreement, and/or in connection with the formation of subsidiaries as contemplated by the Guggenheim Transactions and the Key Transactions (as defined in the Sixth Loan Modification Agreement and the Eleventh Loan Modification Agreement, respectively), have not changed as of the date hereof.

7. CONSISTENT CHANGES. The Existing Loan Documents are hereby amended wherever necessary to reflect the changes described above.

8. RATIFICATION OF LOAN DOCUMENTS. Borrower hereby ratifies, confirms, and reaffirms all terms and conditions of all security or other collateral granted to the Bank, and confirms that the indebtedness secured thereby includes, without limitation, the Obligations.

9. NO DEFENSES OF BORROWER. Borrower hereby acknowledges and agrees that Borrower has no offsets, defenses, claims, or counterclaims against Bank with respect to the Obligations, or otherwise, and that if Borrower now has, or ever did have, any offsets, defenses, claims, or counterclaims against Bank, whether known or unknown, at law or in equity, all of them are hereby expressly WAIVED and Borrower hereby RELEASES Bank from any liability thereunder.

10. CONTINUING VALIDITY. Borrower understands and agrees that in modifying the existing Obligations, Bank is relying upon Borrower’s representations, warranties, and agreements, as set forth in the Existing Loan Documents, after giving effect to this Loan Modification Agreement and the Waiver Agreement entered into between Borrower and Bank dated as of the date hereof. Except as expressly modified pursuant to this Loan Modification Agreement, the terms of the Existing Loan Documents remain unchanged and in full force and effect. Bank’s agreement to modifications to the existing Obligations pursuant to this Loan Modification Agreement in no way shall obligate Bank to make any future modifications to the Obligations. Nothing in this Loan Modification Agreement shall constitute a satisfaction of the Obligations. It is the intention of Bank and Borrower to retain as liable parties all makers of Existing Loan Documents, unless the party is expressly released by Bank in writing.

11. COUNTERSIGNATURE. This Loan Modification Agreement shall become effective only when it shall have been executed by Borrower and Bank.

[Remainder of page intentionally left blank.]

This Loan Modification Agreement “is executed as a sealed instrument under the laws of the Commonwealth of Massachusetts as of the date first written above.

BORROWER:

ASPEN TECHNOLOGY, INC.


By:		/s/
Name:					Xxx X. Xxxxxxx
Title:			Treasurer

BANK:

SILICON VALLEY BANK


By:	/s/
Name:				Xxxxxxx Xxxxxxx
Title:			Senior Vice President

The undersigned, ASPENTECH SECURITIES CORP., a Massachusetts corporation, ratifies, confirms and reaffirms, all and singular, the terms and conditions of a certain Unlimited Guaranty dated January 30, 2003 (the “Guaranty”) and a certain Security Agreement dated as of January 30, 2003 (the “Security Agreement”) and acknowledges, confirms and agrees that the Guaranty and Security Agreement shall remain in full force and effect and shall in no way be limited by the execution of this Loan Modification Agreement, or any other documents, instruments and/or agreements executed and/or delivered in connection herewith.

ASPENTECH SECURITIES CORP.

By:	/s/
Name:			Xxx X. Xxxxxxx
Title:		Treasurer

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FOURTEENTH LOAN MODIFICATION AGREEMENT

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